HU185886B - Process for preparing optically active alpha-cyano-alcohols - Google Patents
Process for preparing optically active alpha-cyano-alcohols Download PDFInfo
- Publication number
- HU185886B HU185886B HU801116A HU111680A HU185886B HU 185886 B HU185886 B HU 185886B HU 801116 A HU801116 A HU 801116A HU 111680 A HU111680 A HU 111680A HU 185886 B HU185886 B HU 185886B
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- cyano
- acid
- optically active
- alcohol
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- -1 cycloaliphatic Chemical group 0.000 claims abstract description 18
- 238000000034 method Methods 0.000 claims abstract description 15
- 229910052796 boron Inorganic materials 0.000 claims abstract description 11
- 150000002148 esters Chemical class 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 5
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims abstract description 4
- 125000003118 aryl group Chemical group 0.000 claims abstract 2
- 239000002253 acid Substances 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 12
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 claims description 8
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims description 6
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 claims description 6
- 239000007858 starting material Substances 0.000 claims description 5
- 150000001735 carboxylic acids Chemical class 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- LLMLSUSAKZVFOA-UHFFFAOYSA-N 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid Chemical class CC1(C)C(C=C(Cl)Cl)C1C(O)=O LLMLSUSAKZVFOA-UHFFFAOYSA-N 0.000 claims description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 238000004587 chromatography analysis Methods 0.000 claims description 2
- 125000003367 polycyclic group Chemical group 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract description 5
- 150000001298 alcohols Chemical class 0.000 abstract description 2
- 229920006395 saturated elastomer Polymers 0.000 abstract description 2
- 125000003158 alcohol group Chemical group 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
- GXUQMKBQDGPMKZ-CQSZACIVSA-N (2s)-2-hydroxy-2-(3-phenoxyphenyl)acetonitrile Chemical compound N#C[C@@H](O)C1=CC=CC(OC=2C=CC=CC=2)=C1 GXUQMKBQDGPMKZ-CQSZACIVSA-N 0.000 description 10
- 238000003756 stirring Methods 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 6
- MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 6
- 239000003480 eluent Substances 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- AFVLVVWMAFSXCK-VMPITWQZSA-N alpha-cyano-4-hydroxycinnamic acid Chemical group OC(=O)C(\C#N)=C\C1=CC=C(O)C=C1 AFVLVVWMAFSXCK-VMPITWQZSA-N 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- PDDSUKSQBULCTG-UHFFFAOYSA-N 2-(3-chlorophenyl)-3-methylbutanoic acid Chemical class CC(C)C(C(O)=O)C1=CC=CC(Cl)=C1 PDDSUKSQBULCTG-UHFFFAOYSA-N 0.000 description 1
- MDIQXIJPQWLFSD-UHFFFAOYSA-N 3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical class CC1(C)C(C=C(Br)Br)C1C(O)=O MDIQXIJPQWLFSD-UHFFFAOYSA-N 0.000 description 1
- SJKVITNXHPKFTD-UHFFFAOYSA-N 3-(cyclobutylidenemethyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical class OC(=O)C1C(C)(C)C1C=C1CCC1 SJKVITNXHPKFTD-UHFFFAOYSA-N 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- 229910015844 BCl3 Inorganic materials 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7914977A FR2458542A1 (fr) | 1979-06-12 | 1979-06-12 | Procede de preparation d'alcools a-cyanes optiquement actifs |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU185886B true HU185886B (en) | 1985-04-28 |
Family
ID=9226467
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU801116A HU185886B (en) | 1979-06-12 | 1980-05-07 | Process for preparing optically active alpha-cyano-alcohols |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4328167A (en, 2012) |
| EP (1) | EP0021925B1 (en, 2012) |
| JP (1) | JPS5612355A (en, 2012) |
| AT (1) | ATE1175T1 (en, 2012) |
| CA (1) | CA1140565A (en, 2012) |
| DE (1) | DE3060522D1 (en, 2012) |
| FR (1) | FR2458542A1 (en, 2012) |
| HU (1) | HU185886B (en, 2012) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ206106A (en) * | 1982-11-22 | 1987-10-30 | Shell Oil Co | Processes for the preparation of optically active cyanomethyl esters of alpha-chiral carboxylic acids and optionally substituted s-alpha-cyano-3-phenoxybenzyl alcohol |
| EP0291626A3 (en) | 1982-11-22 | 1989-05-31 | E.I. Du Pont De Nemours And Company | Process for the preparation of optically-active cyanomethyl esters |
| US4560515A (en) * | 1982-11-22 | 1985-12-24 | Shell Oil Company | Preparation of optically-active cyanomethyl esters |
| JPH037983A (ja) * | 1989-06-05 | 1991-01-16 | Alpine Electron Inc | 地図用記憶媒体の交換方法 |
| JPH03131890A (ja) * | 1989-10-17 | 1991-06-05 | Furuno Electric Co Ltd | 地図表示装置 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2067854A5 (en) * | 1969-11-19 | 1971-08-20 | Roussel Uclaf | Subst vinyl cyclo-propane-1-carboxylic acids insecticidal prepn |
| FR2375161A1 (fr) * | 1976-04-23 | 1978-07-21 | Roussel Uclaf | Procede de transformation d'un ester d'acide chiral d'alcool secondaire a-cyane optiquement actif de structure (r) en ester d'acide chiral d'alcool secondaire a-cyane de structure (s) |
| JPS52144651A (en) * | 1976-05-24 | 1977-12-02 | Sumitomo Chem Co Ltd | Racemization of optical active 2,2-dimethyl-3-(1-alkenyl)-cyclopropane-1-carboxylic acid |
| FR2362829A1 (fr) * | 1976-08-27 | 1978-03-24 | Roussel Uclaf | Combinaison bisulfitique du metaphenoxy benzaldehyde, procede de preparation et application a la preparation de l'alcool a-cyano 3-phenoxy benzylique |
| CH635563A5 (fr) * | 1977-07-07 | 1983-04-15 | Sumitomo Chemical Co | Procede pour la preparation d'un alpha-cyano-3-phenoxybenzyle optiquement actif. |
| ZA7911B (en) * | 1978-01-31 | 1980-01-30 | Roussel Uclaf | Optically-active substituted benzyl alcohol and process for preparing it |
-
1979
- 1979-06-12 FR FR7914977A patent/FR2458542A1/fr active Granted
-
1980
- 1980-05-07 HU HU801116A patent/HU185886B/hu not_active IP Right Cessation
- 1980-06-02 US US06/155,753 patent/US4328167A/en not_active Expired - Lifetime
- 1980-06-06 DE DE8080400809T patent/DE3060522D1/de not_active Expired
- 1980-06-06 EP EP80400809A patent/EP0021925B1/fr not_active Expired
- 1980-06-06 AT AT80400809T patent/ATE1175T1/de active
- 1980-06-11 JP JP7792180A patent/JPS5612355A/ja active Granted
- 1980-06-11 CA CA000353813A patent/CA1140565A/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2458542A1 (fr) | 1981-01-02 |
| US4328167A (en) | 1982-05-04 |
| EP0021925B1 (fr) | 1982-06-09 |
| CA1140565A (fr) | 1983-02-01 |
| DE3060522D1 (en) | 1982-07-29 |
| JPS648617B2 (en, 2012) | 1989-02-14 |
| FR2458542B1 (en, 2012) | 1984-09-28 |
| ATE1175T1 (de) | 1982-06-15 |
| JPS5612355A (en) | 1981-02-06 |
| EP0021925A1 (fr) | 1981-01-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |