*All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
[ 101-43-9 ] Synthesis Path-Downstream 1~45
- 1
- [ 80-62-6 ]
- [ 108-93-0 ]
- [ 101-43-9 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 95% | With lanthanum(III) isopropoxide; 2-(2-methoxyethoxy)ethyl alcohol In hexane Reflux; chemoselective reaction; | |
| 93% | With C2H3O3(1-)*C37H78N(1+) In hexane at 90℃; for 2h; Molecular sieve; | 64 General procedure: In Examples 62 to 64, as shown in Table 13, a transesterification reaction was carried out between methyl methacrylate which is an easily polymerizable ester compound and an alcohol compound. In Example 62, as in Example 24, lanthanum nitrate and tri n-octylphosphine were previously azeotropically refluxed with dimethyl carbonate for 1 hour, then dimethyl carbonate was evaporated at room temperature, The obtained catalyst was used. In Examples 63 and 64, methyltridodecylammonium methyl carbonate was used singly. As a result, ester products were obtained in high yield. It is to be noted that in Example 62, when using the isolated phosphonium salt as a catalyst instead of using the prepared catalyst as it is, it is predicted that the ester product is obtained with a higher yield than in Example 62 . Although not shown in Table 13, potassium tert-butoxide was used as a catalyst, and various by-products were produced. |
| With sodium methylate |
| With di(n-butyl)tin oxide | 21 EXAMPLE 21 Using a reflux apparatus equipped with a 20-plates Oldershaw column as the distillation column, a 3-liter four-necked flask with a side arm was charged with 1,401 g (14 moles) of methyl methacrylate, 701 g (7 moles) of cyclohexanol, 12.6 g of dibutyltin oxide, and 1.18 g (corresponding to 0.1% of the theoretical yield of the product) of IB as a polymerization inhibitor. This mixture was subjected to an ester exchange reaction. The methanol formed as a by-product during reaction was removed from the system together with the methyl methacrylate. The resulting reaction product was purified by simple distillation using an empty column having a length of 20 cm, so that 740 g of cyclohexyl methacrylate was obtained. During the course of the reaction and distillation, polymerization occurred neither in the reactor nor the column. The cyclohexyl methacrylate thus obtained had a color number (APHA) of not greater than 5. | |
| With di(n-butyl)tin oxide | 18 COMPARATIVE EXAMPLE 18 Using a reflux apparatus equipped with a 20-plates Oldershaw column as the distillation column, a 3-liter four-necked flask with a side arm was charged with 1,401 g (14 moles) of methyl methacrylate, 701 g (7 moles) of cyclohexanol, 12.6 g of dibutyltin oxide, and 1.18 g (corresponding to 0.1% of the theoretical yield of the product) of MTX as a polymerization inhibitor. This mixture was subjected to an ester exchange reaction. The methanol formed as a by-product during reaction was removed from the system together with the methyl methacrylate. The resulting reaction product was purified by simple distillation using an empty column having a length of 20 cm, so that 848 g of cyclohexyl methacrylate was obtained. During the course of the reaction and distillation, polymerization occurred neither in the reactor nor the column. However, the cyclohexyl methacrylate thus obtained was slightly colored and had a color number (APHA) of 140. | |
| With toluene-4-sulfonic acid; hydroquinone; benzene zuletzt bei 130-140grad; | ||
| With sulfuric acid; hydroquinone |
Reference： [1]Hatano, Manabu; Furuya, Yoshiro; Shimmura, Takumi; Moriyama, Katsuhiko; Kamiya, Sho; Maki, Toshikatsu; Ishihara, Kazuaki[Organic Letters, 2011, vol. 13, # 3, p. 426 - 429]
[2]Current Patent Assignee: TOKAI NATIONAL HIGHER EDUCATION AND RESEARCH SYSTEM - JP5804472, 2015, B2Location in patent: Paragraph 0087; 0088
[3]Koton; Florinskii[Zhurnal Obshchei Khimii, 1951, vol. 21, p. 1841; engl. Ausg. S. 2041]Navolokina, R. A.; Zil'berman, E. N.; Shtarkman, B. P.; Lunicheva, E. A.[Journal of applied chemistry of the USSR, 1990, vol. 63, # 7.2, p. 1490 - 1493][Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation), 1990, vol. 63, # 7, p. 1614 - 1617]
[4]Tong; Kenyon[Journal of the American Chemical Society, 1946, vol. 68, p. 1355]
[5]Current Patent Assignee: Mitsubishi Chemical Corp (in: MCHC Group); MITSUBISHI CHEMICAL HOLDINGS CORPORATION - US6348598, 2002, B1Location in patent: Page column 12
[6]Current Patent Assignee: Mitsubishi Chemical Corp (in: MCHC Group); MITSUBISHI CHEMICAL HOLDINGS CORPORATION - US6348598, 2002, B1Location in patent: Page column 12-13
[7]Current Patent Assignee: DUPONT DE NEMOURS INC - US2129666, 1934, ACurrent Patent Assignee: DANIEL EUGENE STRAIN; DUPONT DE NEMOURS INC; HAROLD JAMES BARRETT - GB468890, 1935, A
[8]Current Patent Assignee: DOW INC - DE706792, 1937, C[DRP/DRBP Org.Chem.][DRP/DRBP Org.Chem.]
- 2
- [ 50-00-0 ]
- <i>O</i>2,<i>O</i>3-isopropylidene-<i>O</i>5-trityl-<i>D</i>-ribose oxime [ No CAS ]
- [ 101-43-9 ]
- [ 63535-50-2 ]
- [ 63535-49-9 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| (i) CHCl3, (ii) FeCl3, CH2Cl2; Multistep reaction; |
Reference： [1]Vasella,A.[Helvetica Chimica Acta, 1977, vol. 60, p. 426 - 446]
- 3
- [ 101-43-9 ]
- [ 16149-89-6 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With PPA at 100℃; |
Reference： [1]Conia,J.-M.; Leriverend,M.-L.[Bulletin de la Societe Chimique de France, 1970, p. 2981 - 2991]
- 4
- [ 101-43-9 ]
- [ 81622-38-0 ]
- 2,8-Dimethyl-2,3,8,9-tetrahydro-1,7-dioxa-perylene-2,8-dicarboxylic acid dicyclohexyl ester [ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 13% | With copper(I) chloride In water at 25 - 50℃; |
Reference： [1]Fritz; Rihs; Sutter; Weis[Journal of Heterocyclic Chemistry, 1981, vol. 18, # 8, p. 1571 - 1580]
- 5
- [ 101-43-9 ]
- [ 119039-00-8 ]
- [ 119039-12-2 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With 2,2,6,6-tetramethylpiperidinyl-lithium 1.) THF, -78 deg C, 10 min, 2.) -78 deg C, 1 h, 25 deg C, 24 h; Yield given. Multistep reaction; |
Reference： [1]Beak, Peter; Burg, Duglas A.[Journal of Organic Chemistry, 1989, vol. 54, # 7, p. 1647 - 1654]
- 6
- [ 101-43-9 ]
- [ 119070-24-5 ]
- 3-Diisopropylcarbamoyl-1,2-dimethyl-cyclopent-3-enecarboxylic acid cyclohexyl ester [ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With 2,2,6,6-tetramethylpiperidinyl-lithium 1.) THF, -78 deg C, 10 min, 2.) -78 deg C, 1 h, 25 deg C, 24 h; Yield given. Multistep reaction; |
Reference： [1]Beak, Peter; Burg, Duglas A.[Journal of Organic Chemistry, 1989, vol. 54, # 7, p. 1647 - 1654]
- 7
- [ 101-43-9 ]
- [ 119039-17-7 ]
- [ 119039-10-0 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With 2,2,6,6-tetramethylpiperidinyl-lithium 1.) THF, -78 deg C, 10 min, 2.) -78 deg C, 1 h, 25 deg C, 24 h; Yield given. Multistep reaction; |
Reference： [1]Beak, Peter; Burg, Duglas A.[Journal of Organic Chemistry, 1989, vol. 54, # 7, p. 1647 - 1654]
- 8
- [ 101-43-9 ]
- [ 110426-80-7 ]
- [ 110426-81-8 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 89% | With 2,2,6,6-tetramethylpiperidinyl-lithium var. electron-deficient olefins, var. substituted 3-(phenylsulfonyl)propenamides; | |
| With 2,2,6,6-tetramethylpiperidinyl-lithium 1.) -78 grad C, THF, 5 min, 2.) THF, 1 h at -78 grad C, 24 h at room temperature; Yield given. Multistep reaction; | ||
| With 2,2,6,6-tetramethylpiperidinyl-lithium 1.) THF, -78 deg C, 10 min, 2.) -78 deg C, 1 h, 25 deg C, 24 h; Yield given. Multistep reaction; |
Reference： [1]Beak, Peter; Burg, Duglas A.[Journal of Organic Chemistry, 1989, vol. 54, # 7, p. 1647 - 1654]
[2]Beak, Peter; Burg, Douglas A.[Tetrahedron Letters, 1986, vol. 27, # 49, p. 5911 - 5914]
[3]Beak, Peter; Burg, Duglas A.[Journal of Organic Chemistry, 1989, vol. 54, # 7, p. 1647 - 1654]
- 9
- [ 101-43-9 ]
- [ 119039-02-0 ]
- [ 110426-81-8 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With copper(I) bromide dimethylsulfide complex; 2,2,6,6-tetramethylpiperidinyl-lithium 1.) THF, -78 deg C, 10 min, 2.) -78 deg C, 1 h, 25 deg C, 95 h; Yield given. Multistep reaction; |
Reference： [1]Beak, Peter; Burg, Duglas A.[Journal of Organic Chemistry, 1989, vol. 54, # 7, p. 1647 - 1654]
- 10
- [ 101-43-9 ]
- [ 87504-85-6 ]
- [ 119039-13-3 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With 2,2,6,6-tetramethylpiperidinyl-lithium 1.) THF, -78 deg C, 10 min, 2.) -78 deg C, 1 h, 25 deg C, 24 h; Yield given. Multistep reaction; |
Reference： [1]Beak, Peter; Burg, Duglas A.[Journal of Organic Chemistry, 1989, vol. 54, # 7, p. 1647 - 1654]
- 11
- [ 101-43-9 ]
- [ 34900-11-3 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With triethylsilane; [5,10,15,20-tetra(2,6-dichlorophenyl)porphyrinato]cobalt(II); oxygen; phosphorous acid trimethyl ester 1.) 2-propanol, dichloromethane, 28 deg C, 1 atm, 2 h, 2.) 2-propanol, dichloromethane, RT, 2 h; Yield given. Multistep reaction; |
Reference： [1]Matsusita, Yoh-ichi; Sugamoto, Kazuhiro; Matsui, Takanao[Chemistry Letters, 1993, # 6, p. 925 - 928]
- 12
- [ 101-43-9 ]
- 2-[(1-Cyclohexyloxycarbonyl-1-methyl-2-nitro-ethyl)-dioxy-diazenyl]-2-methyl-3-nitro-propionic acid cyclohexyl ester [ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 4% | With sulfuric acid; sodium nitrite In diethyl ether at 0 - 5℃; for 0.5h; |
Reference： [1]Rehse; Herpel[Archiv der Pharmazie, 1998, vol. 331, # 3, p. 111 - 117]
- 13
- [ 101-43-9 ]
- 2-Hydroperoxy-2-methyl-propionic acid cyclohexyl ester [ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 80% | With triethylsilane; oxygen In dichloromethane; isopropyl alcohol at 28℃; for 2h; |
Reference： [1]Sugamoto, Kazuhiro; Matsush*ta, Yoh-Ichi; Matsui, Takanao[Journal of the Chemical Society. Perkin transactions I, 1998, # 23, p. 3989 - 3998]
- 14
- [ 101-43-9 ]
- polymer; monomer: cyclohexyl methacrylate [ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 71.6% | In dichloromethane at 30℃; for 24h; |
Reference： [1]Komiya, Sanshiro; Chigira, Tomoko; Suzuki, Toru; Hirano, Masafumi[Chemistry Letters, 1999, # 4, p. 347 - 348]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Copolym.: r; | ||
| Rk. mit Diazomethan in THF bei 25grad (Verbrauch von Diazomethan gemessen) unter Bildung von 3-Methyl-pyrazol-Δ1 in-3-carbonsaeure-cyclohexylester; | ||
| Polymerisationswaerme; |
| Copolymerisation mit Styrol; | ||
| With perchloric acid; <i>tert</i>-butyl alcohol In water at 25℃; Radiolysis; | ||
| 3 EXAMPLE 3 Test solutions were prepared by adding 5 ppm of each polymerization inhibitor to the various (meth)acrylic esters shown in Table 3 and from which any polymerization inhibitor had previously been removed by distillation. Then, 15 g each of the aforesaid test solutions were poured into 25 ml ampules. These ampules were sealed with silicone stoppers and immersed in an oil bath kept at 700 C. for methyl acrylate (MA), 900 C. for methyl methacrylate (MMA), or 1200 C. for other (meth)acrylic esters. While this oil bath was being shaken on a shaker, the ampules were visually observed to confirm the time at which popcorn formation, gelation or an increase in solution viscosity occurred. Thus, the polymerization initiation time (in minutes) of the (meth)acrylic ester in each ampule was determined. The results thus obtained are also shown in Table 3. | ||
| 5 EXAMPLE 5 Test solutions were prepared by adding 5 ppm of each polymerization inhibitor to the various (meth)acrylic esters shown in Table 3 and from which any polymerization inhibitor had previously been removed by distillation. Then, 15 g each of the aforesaid test solutions were poured into 25 ml ampules. These ampules were sealed with silicone stoppers and immersed in an oil bath kept at 700 C. for methyl acrylate (MA), 900 C. for methyl methacrylate (MMA), or 1200 C. for other (meth)acrylic esters. While this oil bath was being shaken on a shaker, the ampules were visually observed to confirm the time at which popcorn formation, gelation or an increase in solution viscosity occurred. Thus, the polymerization initiation time (in minutes) of the (meth)acrylic ester in each ampule was determined. The results thus obtained are also shown in Table 3. | ||
| 4 EXAMPLE 4 Test solutions were prepared by adding 5 ppm of each polymerization inhibitor to the various (meth)acrylic esters shown in Table 3 and from which any polymerization inhibitor had previously been removed by distillation. Then, 15 g each of the aforesaid test solutions were poured into 25 ml ampules. These ampules were sealed with silicone stoppers and immersed in an oil bath kept at 700 C. for methyl acrylate (MA), 900 C. for methyl methacrylate (MMA), or 1200 C. for other (meth)acrylic esters. While this oil bath was being shaken on a shaker, the ampules were visually observed to confirm the time at which popcorn formation, gelation or an increase in solution viscosity occurred. Thus, the polymerization initiation time (in minutes) of the (meth)acrylic ester in each ampule was determined. The results thus obtained are also shown in Table 3. | ||
| 3 COMPARATIVE EXAMPLE 3 Test solutions were prepared by adding 5 ppm of each polymerization inhibitor to the various (meth)acrylic esters shown in Table 3 and from which any polymerization inhibitor had previously been removed by distillation. Then, 15 g each of the aforesaid test solutions were poured into 25 ml ampules. These ampules were sealed with silicone stoppers and immersed in an oil bath kept at 700 C. for methyl acrylate (MA), 900 C. for methyl methacrylate (MMA), or 1200 C. for other (meth)acrylic esters. While this oil bath was being shaken on a shaker, the ampules were visually observed to confirm the time at which popcorn formation, gelation or an increase in solution viscosity occurred. Thus, the polymerization initiation time (in minutes) of the (meth)acrylic ester in each ampule was determined. The results thus obtained are also shown in Table 3. | ||
| 4 COMPARATIVE EXAMPLE 4 Test solutions were prepared by adding 5 ppm of each polymerization inhibitor to the various (meth)acrylic esters shown in Table 3 and from which any polymerization inhibitor had previously been removed by distillation. Then, 15 g each of the aforesaid test solutions were poured into 25 ml ampules. These ampules were sealed with silicone stoppers and immersed in an oil bath kept at 700 C. for methyl acrylate (MA), 900 C. for methyl methacrylate (MMA), or 1200 C. for other (meth)acrylic esters. While this oil bath was being shaken on a shaker, the ampules were visually observed to confirm the time at which popcorn formation, gelation or an increase in solution viscosity occurred. Thus, the polymerization initiation time (in minutes) of the (meth)acrylic ester in each ampule was determined. The results thus obtained are also shown in Table 3. | ||
| 5 COMPARATIVE EXAMPLE 5 Test solutions were prepared by adding 5 ppm of each polymerization inhibitor to the various (meth)acrylic esters shown in Table 3 and from which any polymerization inhibitor had previously been removed by distillation. Then, 15 g each of the aforesaid test solutions were poured into 25 ml ampules. These ampules were sealed with silicone stoppers and immersed in an oil bath kept at 700 C. for methyl acrylate (MA), 900 C. for methyl methacrylate (MMA), or 1200 C. for other (meth)acrylic esters. While this oil bath was being shaken on a shaker, the ampules were visually observed to confirm the time at which popcorn formation, gelation or an increase in solution viscosity occurred. Thus, the polymerization initiation time (in minutes) of the (meth)acrylic ester in each ampule was determined. The results thus obtained are also shown in Table 3. | ||
| 1 COMPARATIVE EXAMPLE 1 Test solutions were prepared by adding 5 ppm of each polymerization inhibitor to the various (meth)acrylic esters shown in Table 3 and from which any polymerization inhibitor had previously been removed by distillation. Then, 15 g each of the aforesaid test solutions were poured into 25 ml ampules. These ampules were sealed with silicone stoppers and immersed in an oil bath kept at 700 C. for methyl acrylate (MA), 900 C. for methyl methacrylate (MMA), or 1200 C. for other (meth)acrylic esters. While this oil bath was being shaken on a shaker, the ampules were visually observed to confirm the time at which popcorn formation, gelation or an increase in solution viscosity occurred. Thus, the polymerization initiation time (in minutes) of the (meth)acrylic ester in each ampule was determined. The results thus obtained are also shown in Table 3. | ||
| 2 COMPARATIVE EXAMPLE 2 Test solutions were prepared by adding 5 ppm of each polymerization inhibitor to the various (meth)acrylic esters shown in Table 3 and from which any polymerization inhibitor had previously been removed by distillation. Then, 15 g each of the aforesaid test solutions were poured into 25 ml ampules. These ampules were sealed with silicone stoppers and immersed in an oil bath kept at 700 C. for methyl acrylate (MA), 900 C. for methyl methacrylate (MMA), or 1200 C. for other (meth)acrylic esters. While this oil bath was being shaken on a shaker, the ampules were visually observed to confirm the time at which popcorn formation, gelation or an increase in solution viscosity occurred. Thus, the polymerization initiation time (in minutes) of the (meth)acrylic ester in each ampule was determined. The results thus obtained are also shown in Table 3. | ||
| 8 EXAMPLE 8 Test solutions were prepared by adding 5 ppm of each polymerization inhibitor to the various (meth)acrylic esters shown in Table 3 and from which any polymerization inhibitor had previously been removed by distillation. Then, 15 g each of the aforesaid test solutions were poured into 25 ml ampules. These ampules were sealed with silicone stoppers and immersed in an oil bath kept at 700 C. for methyl acrylate (MA), 900 C. for methyl methacrylate (MMA), or 1200 C. for other (meth)acrylic esters. While this oil bath was being shaken on a shaker, the ampules were visually observed to confirm the time at which popcorn formation, gelation or an increase in solution viscosity occurred. Thus, the polymerization initiation time (in minutes) of the (meth)acrylic ester in each ampule was determined. The results thus obtained are also shown in Table 3. | ||
| 6 EXAMPLE 6 Test solutions were prepared by adding 5 ppm of each polymerization inhibitor to the various (meth)acrylic esters shown in Table 3 and from which any polymerization inhibitor had previously been removed by distillation. Then, 15 g each of the aforesaid test solutions were poured into 25 ml ampules. These ampules were sealed with silicone stoppers and immersed in an oil bath kept at 700 C. for methyl acrylate (MA), 900 C. for methyl methacrylate (MMA), or 1200 C. for other (meth)acrylic esters. While this oil bath was being shaken on a shaker, the ampules were visually observed to confirm the time at which popcorn formation, gelation or an increase in solution viscosity occurred. Thus, the polymerization initiation time (in minutes) of the (meth)acrylic ester in each ampule was determined. The results thus obtained are also shown in Table 3. | ||
| 7 EXAMPLE 7 Test solutions were prepared by adding 5 ppm of each polymerization inhibitor to the various (meth)acrylic esters shown in Table 3 and from which any polymerization inhibitor had previously been removed by distillation. Then, 15 g each of the aforesaid test solutions were poured into 25 ml ampules. These ampules were sealed with silicone stoppers and immersed in an oil bath kept at 700 C. for methyl acrylate (MA), 900 C. for methyl methacrylate (MMA), or 1200 C. for other (meth)acrylic esters. While this oil bath was being shaken on a shaker, the ampules were visually observed to confirm the time at which popcorn formation, gelation or an increase in solution viscosity occurred. Thus, the polymerization initiation time (in minutes) of the (meth)acrylic ester in each ampule was determined. The results thus obtained are also shown in Table 3. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 4 EXAMPLE 4 Conversion of HBA: 100 mol % Yield of CHM: 58.4 mol % |
- 17
- [ 101-43-9 ]
- [ 16149-89-6 ]
- 2-methyl-3a,4,5,6,7,7a-hexahydro-inden-1-one [ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With PPA at 100℃; for 1h; |
Reference： [1]Halterman, Ronald L.; Schumann, Herbert; Dübner, Frank[Journal of Organometallic Chemistry, 2000, vol. 604, # 1, p. 12 - 19]
- 18
- [ 101-43-9 ]
- [ 76665-17-3 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Stage #1: cyclohexyl methacrylate With PPA at 100℃; for 1h; Stage #2: With lithium aluminium tetrahydride In diethyl ether at 20℃; for 3h; Stage #3: With hydrogenchloride In water for 1h; Heating; |
Reference： [1]Halterman, Ronald L.; Schumann, Herbert; Dübner, Frank[Journal of Organometallic Chemistry, 2000, vol. 604, # 1, p. 12 - 19]
- 19
- [ 101-43-9 ]
- cis-1H-2-methyl-2,3,4,5,6,7-hexahydroindan-1-ol [ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Stage #1: cyclohexyl methacrylate With PPA at 100℃; for 1h; Stage #2: With lithium aluminium tetrahydride In diethyl ether at 20℃; for 3h; |
Reference： [1]Halterman, Ronald L.; Schumann, Herbert; Dübner, Frank[Journal of Organometallic Chemistry, 2000, vol. 604, # 1, p. 12 - 19]
- 20
- [ 1663-39-4 ]
- [ 3066-71-5 ]
- [ 101-43-9 ]
- poly[(cyclohexyl methacrylate)-random-(cyclohexyl acrylate)]; monomer(s): cyclohexyl methacrylate; cyclohexyl acrylate, weight fraction 0.23; tert-butyl acrylate [ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With dibenzoyl peroxide at 89.85℃; |
Reference： [1]Miwa, Yohei; Sugino, Yusuke; Yamamoto, Katsuhiro; Tanabe, Takuya; Sakaguchi, Masato; Sakai, Masahiro; Shimada, Shigetaka[Macromolecules, 2004, vol. 37, # 16, p. 6061 - 6068]
- 21
- [ 1663-39-4 ]
- [ 3066-71-5 ]
- [ 101-43-9 ]
- poly[(cyclohexyl methacrylate)-random-(cyclohexyl acrylate)]; monomer(s): cyclohexyl methacrylate; cyclohexyl acrylate, weight fraction 0.48; tert-butyl acrylate [ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With dibenzoyl peroxide at 89.85℃; |
Reference： [1]Miwa, Yohei; Sugino, Yusuke; Yamamoto, Katsuhiro; Tanabe, Takuya; Sakaguchi, Masato; Sakai, Masahiro; Shimada, Shigetaka[Macromolecules, 2004, vol. 37, # 16, p. 6061 - 6068]
- 22
- [ 1663-39-4 ]
- [ 3066-71-5 ]
- [ 101-43-9 ]
- poly[(cyclohexyl methacrylate)-random-(cyclohexyl acrylate)]; monomer(s): cyclohexyl methacrylate; cyclohexyl acrylate, weight fraction 0.86; tert-butyl acrylate [ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With dibenzoyl peroxide at 89.85℃; |
Reference： [1]Miwa, Yohei; Sugino, Yusuke; Yamamoto, Katsuhiro; Tanabe, Takuya; Sakaguchi, Masato; Sakai, Masahiro; Shimada, Shigetaka[Macromolecules, 2004, vol. 37, # 16, p. 6061 - 6068]
- 23
- [ 585-07-9 ]
- [ 101-43-9 ]
- poly[(cyclohexyl methacrylate)-random-(tert-butyl methacrylate)]; monomer(s): cyclohexyl methacrylate; tert-butyl methacrylate [ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With dibenzoyl peroxide at 89.85℃; |
Reference： [1]Miwa, Yohei; Sugino, Yusuke; Yamamoto, Katsuhiro; Tanabe, Takuya; Sakaguchi, Masato; Sakai, Masahiro; Shimada, Shigetaka[Macromolecules, 2004, vol. 37, # 16, p. 6061 - 6068]
See Also
Patents Assigned to Pfizer Inc.- 24
- [ 23426-63-3 ]
- [ 585-07-9 ]
- [ 101-43-9 ]
- polymer, atom transfer radical polymerization, random; monomer(s): tert-butyl methacrylate, 1 mol percent; cyclohexyl methacrylate, 100 mol percent; methyl α-bromoisobutyrate [ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With 1,1,4,7,10,10-hexamethyltriethylenetetramine; copper(l) chloride In methoxybenzene at 79.85℃; |
Reference： [1]Miwa, Yohei; Tanabe, Takuya; Yamamoto, Katsuhiro; Sugino, Yusuke; Sakaguchi, Masato; Sakai, Masahiro; Shimada, Shigetaka[Macromolecules, 2004, vol. 37, # 23, p. 8612 - 8617]
- 25
- [ 23877-12-5 ]
- [ 101-43-9 ]
- polymer, atom transfer radical polymerization; monomer(s): tert-butyl α-bromoisobutyrate; cyclohexyl methacrylate [ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With 1,1,4,7,10,10-hexamethyltriethylenetetramine; copper(l) chloride In methoxybenzene at 79.85℃; |
Reference： [1]Miwa, Yohei; Tanabe, Takuya; Yamamoto, Katsuhiro; Sugino, Yusuke; Sakaguchi, Masato; Sakai, Masahiro; Shimada, Shigetaka[Macromolecules, 2004, vol. 37, # 23, p. 8612 - 8617]
- 26
- [ 371255-53-7 ]
- 2,2'-azobis(isovaleronitrile) [ No CAS ]
- [ 101-43-9 ]
- polymer, Dewar benzene repeat unit content: ca. 10 mol %, Mn (SEC): 12900, Mw (SEC): 43500, PDI: 3.37; monomer(s): 2,2'-azobis(isovaleronitrile); cyclohexyl methacrylate; 1,3,4,5,6-pentamethyl-bicyclo[2.2.0]hexa-2,5-dien-2-ylmethyl methacrylate [ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 6.2 g | In chlorobenzene at 65 - 70℃; |
Reference： [1]Gillmore; Neiser; McManus; Roh; Dombrowski; Brown; Dinnocenzo; Farid; Robello[Macromolecules, 2005, vol. 38, # 18, p. 7684 - 7694]
- 27
- [ 594-61-6 ]
- [ 108-93-0 ]
- [ 101-43-9 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 58.4% | at 350℃; Gas phase; |
Reference： [1]Current Patent Assignee: MITSUBISHI GAS CHEMICAL COMPANY INC - EP1186592, 2002, A1Location in patent: Example 4
- 28
- [ 79-41-4 ]
- [ 108-93-0 ]
- [ 101-43-9 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 86% | In water at 120℃; for 24h; |
Reference： [1]Current Patent Assignee: BASF SE - WO2006/87297, 2006, A1Location in patent: Page/Page column 9-12
- 29
- [ 92-84-2 ]
- [ 80-62-6 ]
- [ 101-43-9 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With lithium hydroxide In cyclohexanol | 6.2 (2) (2) Synthesis of methacrylic acid ester In a 1-liter four-necked flask equipped with a stirrer, a thermometer, an air introducing pipe and a rectifying column, 150 g (1.5 moles) of cyclohexanol of the formula: STR7 and 1.0 g of the dried lithium hydroxide were placed. Subsequently, 0.13 g of phenothiazine and 450 g of methyl methacrylate were added thereto with stirring, followed by introduced of air at a rate of 100 ml/min and a temperature rise to carry out the reaction. The reaction was continued while adjusting the reflux ratio so as to make the rectifying column top temperature about 65° C. The column top temperature was raised near the end of the reaction and finally raised to about 100° C. During this time, the temperature of the reaction mixture was 101° C. to 110° C. After 4 hours' reaction, the amount of cyclohexanol used as a starting alcohol became 0.3% by weight (calculated from the areas of gas chromatogram in percentage) based on the total of the alcohol and the desired product of methacrylic acid ester, and the reaction was finished. The reaction mixture was subjected to distillation under reduced pressure to remove the methyl methacrylate, followed by cooling to room temperature. Then, the reaction mixture was subjected to suction filtration using a Buchner funnel with a filtering area of 70 cm2 and using an aspirator. As a result, 225 g of cyclohexyl methacrylate was yielded. The time required for the filtration was 2 minutes 40 seconds. |
Reference： [1]Current Patent Assignee: SHOWA DENKO K K; Showa Denko Materials (in: Showa Denko) - US5072027, 1991, A
- 30
- [ 32109-09-4 ]
- [ 101-43-9 ]
- [ 100351-41-5 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 14% | In neat (no solvent) byproducts: cyclohexyl isobutyrate, poly(cyclohexyl methacrylate), H2; CH2=CMeCOOC6H11 was added by trap-to-trap method to MoH4(dppe)2, mixt. was heated at 100°C in vacuo for 8 h; mixt. was dried, residue extd. with hexane, ext. evapd., residue recrystd. from Et2O; elem. anal. for Mo-complex, formation of Me2CHCOO-cyclo-C6H11 and H2 was confirmed by GLC; |
Reference： [1]Ito, Takashi; Tosaka, Hisao; Yoshida, Shun-Ji; Mita, Katsuhisa; Yamamoto, Akio[Organometallics, 1986, vol. 5, # 4, p. 735 - 739]
- 31
- [ 78-85-3 ]
- [ 108-93-0 ]
- [ 101-43-9 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Stage #1: 2-methylpropenal With tert-butylhypochlorite In tetrachloromethane at 20 - 50℃; for 5.5 - 6.5h; Stage #2: cyclohexanol In tetrachloromethane at 0 - 20℃; for 2h; | 16 The procedure of Example 12 was repeated except 7.145 g of cyclohexanol was used instead of n-butanol. The process conditions and yield are shown in Table 2.; TABLE 2 Diol/ Reaction Time Yield Example Methacrylate Alcohol Conditions (hr.) (%) 12 n-butyl n- same as 18.5 56.3 methacrylate butanol Example 11 13 t-butyl t- added TEA 19.5 57.4 methacrylate butanol 14 allyl allyl same as 15.5 88.1 methacrylate alcohol Example 11 15 2-ethylhexyl 2-ethyl same as 1.5 69.8 methacrylate hexanol Example 11 16 cyclohexyl cyclohex same as 2 47.4 methacrylate anol Example 11 17 phenyl phenol same as 2 50.4 methacrylate Example 11 18 glycidyl glycidol same as 2.5 41.1 methacrylate Example 11 |
Reference： [1]Current Patent Assignee: GOVERNMENT OF SAUDI ARABIA; ARAMCO (in: Saudi Arabia Government); SABIC (in: Saudi Arabia Government) - US2003/216587, 2003, A1Location in patent: Page/Page column 4
- 32
- [ 79-41-4 ]
- [ 101-43-9 ]
- poly(cyclohexyl methacrylate-co-methacrylic acid) [ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 83% | With tert-butylperoxy 2-ethylhexanoate; butanone at 80℃; for 8h; | 2.1 260 g of methyl ethyl ketone are placed in a three-necked flask equipped with a magnetic bar, followed by the monomers, 42.5 g of cyclohexyl methacrylate and 7.5 g of methacrylic acid. A stream of nitrogen is circulated in the flask for a few minutes so as to remove the ambient oxygen. Finally, the initiator is introduced, 155 μL of Trigonox 21S (t-butylperoxy 2-ethylhexanoate). The reaction medium is then heated in an oil bath at 80° C. for 8 hours. A viscous product is obtained. The polymer is precipitated by adding the reaction medium dropwise to 4 l of methanol with stirring. The polymer is recovered by filtration and then dried under vacuum. 83% yield. Composition by NMR: 83.7% cyclohexyl methacrylate, 16.3% methacrylic acid Mass by GPC in THF (polystyrene standards): Mp=134,315 g.mol-1; Mn=85,905 g.mol-1; Mw=159,093 g.mol-1 Ip=1.85 2nd step: Dispersion of the Polymer in Water 40 g of the above polymer are dissolved in 220 g of tetrahydrofuran. The acid functions are neutralized by adding 6.75 g of 2-amino-2-methylpropanol. 160 g of water are then added to the medium, and the tetrahydrofuran is evaporated off under reduced pressure on a rotary evaporator. After evaporation, an opalescent dispersion at 22% by mass in water is obtained. |
Reference： [1]Current Patent Assignee: L'OREAL SA - US2007/92473, 2007, A1Location in patent: Page/Page column 9-10
- 33
- [ 101-43-9 ]
- cyclohexyl 2-methyl-3-nitroacrylate [ No CAS ]
- [ 1310686-73-7 ]
- [ 1310686-67-9 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 36% | With tetranitromethane; triethylamine In 1,4-dioxane at 70℃; for 4h; | Procedure A: alkene nitration: General procedure: Et3N (0.28 mL, 2 mmol) was added dropwise to a solution of tetranitromethane (0.30 mL, 2.5 mmol) in 1,4-dioxane (2 mL) at 0 oC (ice bath). The reaction mixture was stirred for 5 min after which the alkene (1 mmol) was added in one portion. The mixture was stirred at 70 oC for 4 h. TLC and NMR spectra were used to monitor the progress of the reaction. The solvent was removed under reduced pressure and the product was isolated by column chromatography (petroleum ether - EtOAc, 10:1). |
Reference： [1]Volkova, Yulia A.; Averina, Elena B.; Grishin, Yuri K.; Rybakov, Victor B.; Kuznetsova, Tamara S.; Zefirov, Nikolai S.[Tetrahedron Letters, 2011, vol. 52, # 22, p. 2910 - 2913]
- 34
- [ 101-43-9 ]
- cyclohexyl 2-methyl-3-nitroacrylate [ No CAS ]
- [ 1310686-73-7 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 2 steps1.1: tetranitromethane; triethylamine / 1,4-dioxane / 4 h / 70 °C2.1: methanesulfonyl chloride / dichloromethane / 0.25 h / -20 °C2.2: 6 h / -20 - 20 °C |
Reference： [1]Volkova, Yulia A.; Averina, Elena B.; Grishin, Yuri K.; Rybakov, Victor B.; Kuznetsova, Tamara S.; Zefirov, Nikolai S.[Tetrahedron Letters, 2011, vol. 52, # 22, p. 2910 - 2913]
- 35
- [ 110-89-4 ]
- [ 101-43-9 ]
- C15H27NO2 [ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 72.8% | In toluene at 65℃; for 36h; | 1 Example 1 Example 1 After 16.8 g (100 mmol) of cyclohexyl methacrylate, 25.6 g (300 mmol) of piperidine and 20 g of toluene were charged into a 100 mL eggplant-shaped flask, and the mixture was heated at 65° C. for 36 hour with stirring to allow the reaction to proceed. After completion of the reaction, water was added to the reaction liquid, and the organic layer was washed with water seven times by liquid separating operation. Next, the organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off to give a light yellow oily matter. The oily matter was purified on column chromatography to obtain 18.4 g (yield: 72.8%) of a compound represented by the following formula (i-1) as colorless oily matter. |
Reference： [1]Current Patent Assignee: JSR CORPORATION - US9588423, 2017, B2Location in patent: Page/Page column 58
- 36
- [ 101-43-9 ]
- [ 120-46-7 ]
- cyclohexyl 2-methyl-4-benzoylbutyrate [ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 14% | With potassium carbonate at 85℃; for 48h; | 9 Preparation of cyclohexyl 2-methyl-4-benzoylbutyrate(Compound III-9) To the 20 mL reaction tube was added 112 mg (0.5 mmol) of compound dibenzoylmethane, 7 mg (0.025 mmol) of K2CO3, 174 μL (1 mmol) of cyclohexyl methacrylate and 0.5 mL of ethanol or cyclohexanol, The reaction was stirred at 48 ° C for 48 hours, cooled to room temperature and transferred to a small flask of 10 mL. The solvent was distilled off under reduced pressure and then passed through a column of neutral alumina. The developing solvent used was petroleum ether: ethyl acetate = 20: 1 To 6: 1, i.e., compound III-9 20 mg or 17 mg, yield 14% or 12%. |
Reference： [1]Current Patent Assignee: SOUTHWEST UNIVERSITY - CN105061125, 2017, BLocation in patent: Paragraph 0069-0071
- 37
- [ 101-43-9 ]
- [ 829-85-6 ]
- C22H27O2P [ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 82% | In 2-methyltetrahydrofuran at 90℃; for 4h; Inert atmosphere; Sealed tube; Green chemistry; regioselective reaction; |
Reference： [1]Bissessar, Damien; Egly, Julien; Achard, Thierry; Steffanut, Pascal; Bellemin-Laponnaz, Stéphane[RSC Advances, 2019, vol. 9, # 47, p. 27250 - 27256]
- 38
- [ 101-43-9 ]
- CuI-diphenylphosphine complex [ No CAS ]
- C88H108Cu4I4O8P4 [ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| at 70℃; for 7h; Schlenk technique; Inert atmosphere; | C Process C) General procedure: Cul-diphenylphosphine complex was dissolved in dry acetonitrile (or CH2CI2) and placed in a flame-dried Schlenck tube under argon. The acrylate derivative was added and the solution was heated at 70°C during 7 hours. Then the mixture was cooldown to the room temperature and the solvent was removed under vacuum. The solid residue was dissolve in CH2CI2 and the solution was poured into Et20. The complex precipitates directly and was filtrate and washed several times with Et20 and hexane. The product was dried under vacuum. |
Reference： [1]Current Patent Assignee: CLARIANT AG - WO2019/243583, 2019, A1Location in patent: Page/Page column 39; 42; 49
- 39
- [ 101-43-9 ]
- [ 611-73-4 ]
- C17H22O3 [ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 72% | With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; potassium <i>tert</i>-butylate In acetonitrile at 20℃; Inert atmosphere; Sealed tube; Irradiation; |
Reference： [1]Zhang, Hong; Xiao, Qian; Qi, Xu-Kuan; Gao, Xue-Wang; Tong, Qing-Xiao; Zhong, Jian-Ji[Chemical Communications, 2020, vol. 56, # 83, p. 12530 - 12533]
- 40
- [ 45842-10-2 ]
- [ 101-43-9 ]
- C19H33NO3 [ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| at 150℃; for 48h; Inert atmosphere; | 1 Cyclohexyl methacrylate and 2,2,6,6-tetramethylpiperi in a nitrogen atmosphere The gin-1-oxyl radical was mixed and the resulting mixture was heated at 150 ° C. for 48 hours. .. In addition, cyclohexyl methacrylate and 2,2,6,6-tetramethylpiperidine-1 The mixed molar ratio with the -oxyl radical was 1: 2. Silica gel column chromatography (eluent: hexane / ethyl acetate = 40/1) An alkoxyamine compound represented by the following formula from the product obtained by the separation treatment used ( Compound 1) was obtained. |
Reference： [1]Current Patent Assignee: GOTO IKUEIKAI - JP2021/1134, 2021, ALocation in patent: Paragraph 0056-0058; 0160-0161
- 41
- [ 696-63-9 ]
- [ 101-43-9 ]
- cyclohexyl 2-hydroxy-3-((4-methoxyphenyl)thio)-2-methylpropanoate [ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 71% | With oxygen; N-ethyl-N,N-diisopropylamine In 1,2-dichloro-ethane at 20℃; Irradiation; |
Reference： [1]Shi, Jing; Gao, Xue-Wang; Tong, Qing-Xiao; Zhong, Jian-Ji[Journal of Organic Chemistry, 2021, vol. 86, # 18, p. 12922 - 12931]
- 42
- [ 3340-78-1 ]
- [ 101-43-9 ]
- C25H29NO2 [ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 63% | With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; chloropyridinecobaloxime(III) In dimethyl sulfoxide at 20℃; Inert atmosphere; Sealed tube; Irradiation; |
Reference： [1]Tong, Qing-Xiao; Xu, Hui; Zhang, Hong; Zhong, Jian-Ji[Organic and Biomolecular Chemistry, 2021, vol. 19, # 38, p. 8227 - 8231]
- 43
- [ 355-43-1 ]
- [ 101-43-9 ]
- 4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-2-hydroxy-2-methylnonanoic acid cyclohexyl ester [ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 34% | With pyrrolidine; Diphenylacetaldehyde; oxygen In ethanol; water at 20℃; for 16h; Inert atmosphere; Irradiation; | 48 Example 8 Preparation of 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-1-phenyl-1-octanol (b) General procedure: Add diphenylacetaldehyde (45.0 mg, 0.50 mmol, 1.0 equiv.) To a 20 mL two-necked eggplant-shaped flask equipped with a stir bar, reduce the pressure with a vacuum pump, and then return to normal pressure with argon. I went there times. To this, 1,2-dichloroethane (2.5 mL), styrene (29 μL, 0.25 mmol) and pyrrolidine (44 μL, 0.53 mmol, 2.1 equiv.),1-Iodotridecafluorohexane (180 μL, 0.75 mmol, 3.3 equiv.) And water (25 μL, 5.0 equiv.) Were charged, and light irradiation was carried out with a 23 W-CFL lamp for 16 hours at room temperature with stirring. rice field.After completion of the reaction, a crude product was obtained by concentrating with an evaporator, and the yield of the target product was calculated by 19F-NMR measurement using trifluoromethylbenzene as an internal standard substance.The yield of the target product was 41%.The target product 3,3,4,4,5,5,6,6,7,7 purified and isolated by silica gel column chromatography (hexane / ethyl acetate = 10/1 to 8/1 vol / vol). , 8,8,8-Tridecafluoro-1-phenyl-1-octanol (b) had the following analytical values. |
Reference： [1]Current Patent Assignee: OCHANOMIZU UNIVERSITY; TOSOH CORPORATION - JP2021/134205, 2021, ALocation in patent: Paragraph 0122-0125; 0137-0139
- 44
- [ 101-43-9 ]
- [ 611-73-4 ]
- cyclohexyl 2-benzoyl-2-methyl-4-oxo-4-phenylbutanoate [ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 40% | With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; tetrabutylammonium nitrate In 1,2-dimethoxyethane at 20℃; for 24h; Irradiation; Sealed tube; Inert atmosphere; |
Reference： [1]Chen, Bin; Cheng, Yuan-Yuan; Hou, Hong-Yu; Lei, Tao; Tung, Chen-Ho; Wu, Li-Zhu; Yu, Ji-Xin[Angewandte Chemie - International Edition, 2021, vol. 60, # 51, p. 26822 - 26828][Angew. Chem., 2021, vol. 133, # 51, p. 27026 - 27032]
- 45
- [ 3296-07-9 ]
- [ 101-43-9 ]
- cyclohexyl 1-(2-chlorophenyl)-2-methylaziridine-2-carboxylate [ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 70% | In toluene at 110℃; for 24h; |
Reference： [1]Sebest, Filip; Radtanajiravong, Lalita; Kaukver, Siim; White, Andrew J. P.; Díez-González, Silvia[Chemical Communications, 2022, vol. 58, # 22, p. 3681 - 3684]
