GB2008589A - Optical resolution process - Google Patents
Optical resolution processInfo
- Publication number
- GB2008589A GB2008589A GB7845700A GB7845700A GB2008589A GB 2008589 A GB2008589 A GB 2008589A GB 7845700 A GB7845700 A GB 7845700A GB 7845700 A GB7845700 A GB 7845700A GB 2008589 A GB2008589 A GB 2008589A
- Authority
- GB
- United Kingdom
- Prior art keywords
- cis
- isomers
- mixture
- isomer
- esters
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000000034 method Methods 0.000 title abstract 2
- 230000003287 optical effect Effects 0.000 title 1
- 239000000203 mixture Substances 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 3
- 230000000694 effects Effects 0.000 abstract 3
- 150000002148 esters Chemical class 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 abstract 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 abstract 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 239000011737 fluorine Substances 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 230000000749 insecticidal effect Effects 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 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
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/487—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Esters of cyclopropane carboxylic acids of formula I <IMAGE> where X and Y are independently selected from fluorine, chlorine and bromine have insecticidal activity. Esters of the cis-isomers have superior activity and esters of the 1R-cis-acids have the greatest activity. The process of the invention effects separation of the 1R-cis-isomer from a mixture of 1R- and 1S-cis-isomers of formula (I) by the steps of:- (a) reacting the mixture of isomers with (-)-quinine to give the corresponding salts of the two isomers in the mixture, (b) selectivity crystallising out the quinine salt of the 1 R-cis-isomer from a C1-6 alkanol/water mixture and separating out the resulting crystallised salt, and (c) liberating the 1 R-cis-isomer of the acid of formula (I) from the resulting crystallised salt by means of dilute mineral acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7845700A GB2008589B (en) | 1977-11-23 | 1978-11-23 | Optical resolution process |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4875477 | 1977-11-23 | ||
| GB7845700A GB2008589B (en) | 1977-11-23 | 1978-11-23 | Optical resolution process |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2008589A true GB2008589A (en) | 1979-06-06 |
| GB2008589B GB2008589B (en) | 1982-03-10 |
Family
ID=26266325
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7845700A Expired GB2008589B (en) | 1977-11-23 | 1978-11-23 | Optical resolution process |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB2008589B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4229593A (en) * | 1979-05-29 | 1980-10-21 | Fmc Corporation | Method to prepare (+)-cis-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic acid |
| EP0034428A3 (en) * | 1980-01-31 | 1981-09-09 | Sumitomo Chemical Company, Limited | A method of preparing an optically active cyclo-propanecarboxylic acid and a novel salt used in this method |
-
1978
- 1978-11-23 GB GB7845700A patent/GB2008589B/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4229593A (en) * | 1979-05-29 | 1980-10-21 | Fmc Corporation | Method to prepare (+)-cis-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic acid |
| EP0034428A3 (en) * | 1980-01-31 | 1981-09-09 | Sumitomo Chemical Company, Limited | A method of preparing an optically active cyclo-propanecarboxylic acid and a novel salt used in this method |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2008589B (en) | 1982-03-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |