GB797184A - Improvements in the production of cycloheptene-(1)-carboxylic acid-(1), its alkali metal salts and its esters - Google Patents

Improvements in the production of cycloheptene-(1)-carboxylic acid-(1), its alkali metal salts and its esters

Info

Publication number
GB797184A
GB797184A GB33640/56A GB3364056A GB797184A GB 797184 A GB797184 A GB 797184A GB 33640/56 A GB33640/56 A GB 33640/56A GB 3364056 A GB3364056 A GB 3364056A GB 797184 A GB797184 A GB 797184A
Authority
GB
United Kingdom
Prior art keywords
octanone
alkali metal
cycloheptene
per cent
carboxylic acid
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.)
Expired
Application number
GB33640/56A
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.)
BASF SE
Original Assignee
BASF SE
Badische Anilin and Sodafabrik AG
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 BASF SE, Badische Anilin and Sodafabrik AG filed Critical BASF SE
Publication of GB797184A publication Critical patent/GB797184A/en
Expired legal-status Critical Current

Links

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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
    • C07C45/676—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton by elimination of carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C67/347—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to unsaturated carbon-to-carbon bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Cycloheptene-(1)-carboxylic acid-(1), its alkali metal salts and its esters with aliphatic alcohols are prepared by treating a 2,8-dihalocyclo-octanone with an alkali metal alcoholate or hydroxide in the presence of an inert medium which does not react with the alkali metal compound, and if required acidifying the product to obtain the free acid. Preferred media for use with alkali metal alcoholates are the corresponding alcohols, when the product is the corresponding ester of cycloheptene-1-carboxylic acid, and using alkali metal hydroxides, water, when the alkali metal salt of the acid is obtained; other specified media are ethers and hydrocarbons. It is preferred to use at least 2 mols. of hydroxide or alcoholate per mol. of 2,8-dihalocyclo-octanone (at least 3 mols. per mol. when alkali metal salts are required), the concentration of hydroxide or alcoholate being between 1 and 50 per cent by weight, particularly between 3 and 10 per cent. In examples: (1) and (3) 2,8-dibromocyclo-octanone is stirred with 10 per cent aqueous KOH at 5 DEG C., the mixture acidified and cycloheptene-1-carboxylic acid-(1) isolated by ether extraction; (2) as in (1) but refluxing the octanone with 50 per cent KOH solution; (4) 2,8-di chlorocyclo-octanone and 10 per cent NaOH are reacted as in (1); (5) 2,8-dibromocyclo-octanone is added to 10 per cent sodium methylate in methanol at 5 DEG C., the mixture acidified and the methyl ester of cycloheptene-1-carboxylic acid-(1) isolated by vacuum distillation; (6) to (8) similarly using KOH in ethanol, sodium butylate in butanol, and KOH in cyclohexanol, are obtained the corresponding ethyl, butyl, and cyclohexyl esters. Starting materials 2,8-dichlorocyclo-octanone and 2,8-dibromocyclo-octanone are prepared by direct halogenation of cyclo-octanone in carbon tetrachloride.
GB33640/56A 1955-12-06 1956-11-05 Improvements in the production of cycloheptene-(1)-carboxylic acid-(1), its alkali metal salts and its esters Expired GB797184A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE797184X 1955-12-06

Publications (1)

Publication Number Publication Date
GB797184A true GB797184A (en) 1958-06-25

Family

ID=6711119

Family Applications (1)

Application Number Title Priority Date Filing Date
GB33640/56A Expired GB797184A (en) 1955-12-06 1956-11-05 Improvements in the production of cycloheptene-(1)-carboxylic acid-(1), its alkali metal salts and its esters

Country Status (1)

Country Link
GB (1) GB797184A (en)

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