GB2008110A - Process for cyclising phi - chlorocarboxylic acid esters - Google Patents

Process for cyclising phi - chlorocarboxylic acid esters

Info

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Withdrawn
Application number
GB7843736A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Evonik Operations GmbH
Original Assignee
Degussa GmbH
Deutsche Gold und Silber Scheideanstalt
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Degussa GmbH, Deutsche Gold und Silber Scheideanstalt filed Critical Degussa GmbH
Publication of GB2008110A publication Critical patent/GB2008110A/en
Withdrawn legal-status Critical Current

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.
GB7843736A 1977-11-16 1978-11-08 Process for cyclising phi - chlorocarboxylic acid esters Withdrawn GB2008110A (en)

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)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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

Cited By (16)

* Cited by examiner, † Cited by third party
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
BE872029A (en) 1979-05-14
JPS5479254A (en) 1979-06-25
IL55932A0 (en) 1979-01-31
NL7808602A (en) 1979-05-18
IT1109289B (en) 1985-12-16
DE2751133A1 (en) 1979-05-17
FR2409255A1 (en) 1979-06-15
IT7851913A0 (en) 1978-11-15

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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)