GB2008110A - Process for cyclising phi - chlorocarboxylic acid esters - Google Patents
Process for cyclising phi - chlorocarboxylic acid estersInfo
- Publication number
- GB2008110A GB2008110A GB7843736A GB7843736A GB2008110A GB 2008110 A GB2008110 A GB 2008110A GB 7843736 A GB7843736 A GB 7843736A GB 7843736 A GB7843736 A GB 7843736A GB 2008110 A GB2008110 A GB 2008110A
- Authority
- GB
- United Kingdom
- Prior art keywords
- esters
- phi
- represent
- general formula
- reaction
- 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.)
- Withdrawn
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C69/757—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
phi -Chlorocarboxylic acid esters corresponding to the general formula <IMAGE> in which R, R1, R2, R3, R4 and R5, which may be the same or different, each represent a linear or branched alkyl radical containing from 1 to 4 carbon atoms or, except for R, may also represent a hydrogen atom, are cyclised to form an optionally substituted cyclopropane carboxylic acid or an ester thereof corresponding to the general formula <IMAGE> in which the symbols R to R5 are as defined above, by reaction with an anhydrous alkali metal alcoholate as condensation agent, in an inert organic solvent, the alcohol formed during the reaction being continuously distilled off; the esters produced being optionally hydrolysed to obtain the free acids. The cyclopropane carboxylic acids and their esters which can be produced according to the invention are valuable intermediates for the production of agricultural chemicals, particularly herbicides, and pharmaceutical chemicals. The process according to the invention allows yields of 90 % or more to be obtained.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19772751133 DE2751133A1 (en) | 1977-11-16 | 1977-11-16 | PROCESS FOR CYCLIZING GAMMA CHLOROCARBON ACID ESTERS |
Publications (1)
Publication Number | Publication Date |
---|---|
GB2008110A true GB2008110A (en) | 1979-05-31 |
Family
ID=6023826
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB7843736A Withdrawn GB2008110A (en) | 1977-11-16 | 1978-11-08 | Process for cyclising phi - chlorocarboxylic acid esters |
Country Status (8)
Country | Link |
---|---|
JP (1) | JPS5479254A (en) |
BE (1) | BE872029A (en) |
DE (1) | DE2751133A1 (en) |
FR (1) | FR2409255A1 (en) |
GB (1) | GB2008110A (en) |
IL (1) | IL55932A0 (en) |
IT (1) | IT1109289B (en) |
NL (1) | NL7808602A (en) |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2467190A1 (en) * | 1979-10-11 | 1981-04-17 | Degussa | PROCESS FOR CYCLING GAMMA-CHLOROCARBOXYL ESTERS |
US4348535A (en) * | 1979-12-22 | 1982-09-07 | Dynamit Nobel Ag | Substituted lactones and processes for their preparation |
EP0219652A2 (en) * | 1985-10-24 | 1987-04-29 | Degussa Aktiengesellschaft | Process for the preparation of 1-methylcyclopropanecarboxaldehyde |
EP0220412A2 (en) * | 1985-10-26 | 1987-05-06 | Hüls Aktiengesellschaft | Process for the preparation of pure, chlorine-free cyclopropanecarboxylic-acid esters |
EP0577949A1 (en) * | 1992-07-09 | 1994-01-12 | Hüls Aktiengesellschaft | Method of preparing chlorine free cyclopropanecarbocylicacid methylester |
EP0844242A1 (en) * | 1996-11-26 | 1998-05-27 | Daicel Chemical Industries, Ltd. | Method of producing 4-hydroxy-2-pyrrolidinone and method of purifying the same |
US6252089B1 (en) | 1997-11-25 | 2001-06-26 | Daicel Chemical Industries, Ltd. | Method of producing 4-hydroxy-2-pyrrolidinone and method of purifying the same |
WO2002010116A2 (en) * | 2000-08-01 | 2002-02-07 | Eastman Chemical Company | Process for the preparation of alkyl 1-methylcyclopropanecarboxylate |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB8615313D0 (en) * | 1986-06-23 | 1986-07-30 | Ici Plc | Chemical process |
CA2056840A1 (en) * | 1990-12-17 | 1992-06-18 | Thomas Meul | Process for the production of dimethylcyclopropanecarboxylic acid |
-
1977
- 1977-11-16 DE DE19772751133 patent/DE2751133A1/en active Pending
-
1978
- 1978-08-18 NL NL7808602A patent/NL7808602A/en not_active Application Discontinuation
- 1978-11-08 GB GB7843736A patent/GB2008110A/en not_active Withdrawn
- 1978-11-10 FR FR7831874A patent/FR2409255A1/en not_active Withdrawn
- 1978-11-14 IL IL55932A patent/IL55932A0/en unknown
- 1978-11-14 BE BE6046669A patent/BE872029A/en unknown
- 1978-11-14 JP JP13948078A patent/JPS5479254A/en active Pending
- 1978-11-15 IT IT51913/78A patent/IT1109289B/en active
Cited By (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2467190A1 (en) * | 1979-10-11 | 1981-04-17 | Degussa | PROCESS FOR CYCLING GAMMA-CHLOROCARBOXYL ESTERS |
US4520209A (en) * | 1979-10-11 | 1985-05-28 | Degussa Aktiengesellschaft | Process for cyclizing upsilon-chlorocarboxylic acids |
US4348535A (en) * | 1979-12-22 | 1982-09-07 | Dynamit Nobel Ag | Substituted lactones and processes for their preparation |
EP0219652A2 (en) * | 1985-10-24 | 1987-04-29 | Degussa Aktiengesellschaft | Process for the preparation of 1-methylcyclopropanecarboxaldehyde |
EP0219652A3 (en) * | 1985-10-24 | 1988-10-05 | Degussa Aktiengesellschaft | Process for the preparation of 1-methylcyclopropanecarboxaldehyde |
EP0220412A2 (en) * | 1985-10-26 | 1987-05-06 | Hüls Aktiengesellschaft | Process for the preparation of pure, chlorine-free cyclopropanecarboxylic-acid esters |
EP0220412A3 (en) * | 1985-10-26 | 1989-04-26 | Huls Aktiengesellschaft | Process for the preparation of pure, chlorine-free cyclopropanecarboxylic-acid esters |
US5371270A (en) * | 1992-07-09 | 1994-12-06 | Huels Aktiengesellschaft | Method of manufacturing chlorine-free cyclopropanecarboxylic acid methyl ester |
EP0577949A1 (en) * | 1992-07-09 | 1994-01-12 | Hüls Aktiengesellschaft | Method of preparing chlorine free cyclopropanecarbocylicacid methylester |
EP0844242A1 (en) * | 1996-11-26 | 1998-05-27 | Daicel Chemical Industries, Ltd. | Method of producing 4-hydroxy-2-pyrrolidinone and method of purifying the same |
US6031113A (en) * | 1996-11-26 | 2000-02-29 | Daicel Chemical Industries, Ltd. | Method of producing 4-hydroxy-2-pyrrolidinone and method of purifying the same |
US6153766A (en) * | 1996-11-26 | 2000-11-28 | Daicel Chemical Industries, Ltd. | Method of producing 4-hydroxy-2-pyrrolidinone and method of purifying the same |
US6252089B1 (en) | 1997-11-25 | 2001-06-26 | Daicel Chemical Industries, Ltd. | Method of producing 4-hydroxy-2-pyrrolidinone and method of purifying the same |
WO2002010116A2 (en) * | 2000-08-01 | 2002-02-07 | Eastman Chemical Company | Process for the preparation of alkyl 1-methylcyclopropanecarboxylate |
WO2002010116A3 (en) * | 2000-08-01 | 2002-05-10 | Eastman Chem Co | Process for the preparation of alkyl 1-methylcyclopropanecarboxylate |
US6552217B2 (en) | 2000-08-01 | 2003-04-22 | Eastman Chemical Company | Process for the preparation of alkyl 1-methylcyclopropanecarboxylate |
Also Published As
Publication number | Publication date |
---|---|
IT1109289B (en) | 1985-12-16 |
DE2751133A1 (en) | 1979-05-17 |
BE872029A (en) | 1979-05-14 |
IT7851913A0 (en) | 1978-11-15 |
FR2409255A1 (en) | 1979-06-15 |
IL55932A0 (en) | 1979-01-31 |
NL7808602A (en) | 1979-05-18 |
JPS5479254A (en) | 1979-06-25 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
WAP | Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1) |