GB907431A - Improvements in or relating to alicyclic keto-esters and process for their manufacture - Google Patents

Improvements in or relating to alicyclic keto-esters and process for their manufacture

Info

Publication number
GB907431A
GB907431A GB681461A GB681461A GB907431A GB 907431 A GB907431 A GB 907431A GB 681461 A GB681461 A GB 681461A GB 681461 A GB681461 A GB 681461A GB 907431 A GB907431 A GB 907431A
Authority
GB
United Kingdom
Prior art keywords
methyl
oxo
alkyl
prepared
ethyl
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
GB681461A
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.)
Individual
Original Assignee
Individual
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
Priority claimed from CH212160A external-priority patent/CH382731A/en
Priority claimed from CH856360A external-priority patent/CH490313A/en
Application filed by Individual filed Critical Individual
Publication of GB907431A publication Critical patent/GB907431A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61Preparation 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
    • C07C45/63Preparation 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 introduction of halogen; by substitution of halogen atoms by other halogen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/45Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C07C45/455Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation with carboxylic acids or their derivatives
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61Preparation 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
    • C07C45/67Preparation 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
    • C07C45/68Preparation 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 increase in the number of carbon atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises compounds of the general formula <FORM:0907431/IV (b)/1> wherein R1 represents a methyl or ethyl group, R represents an alkyl radical containing 4 to 6 carbon atoms and n represents 1 or 2; and a process for their preparation by condensing a 2-alkyl-2-cyclo-pentene or hexene-1 one with a lower dialkyl malonate in the presence of a basic condensing agent, saponifying and decarboxylating the resulting dialkyl-2-alkyl-3-oxo-cycloalkyl malonate and esterifying the resulting 2-alkyl-3-oxo-cycloalkyl acetic acid to give the desired methyl or ethyl ester. The process is preferably effected by condensing the ketone and malonate in the presence of sodium ethoxide, heating the resulting adduct with a mixture of acetic and hydrochloric acids to effect saponification and decarboxylation and esterifying the resulting acid with the appropriate alcohol. Examples describe the preparation of the methyl and ethyl esters of 2-n-butyl-, n and iso-amyl- and n-hexyl-3-oxo-cyclopentyl acetic acid and 2-n-amyl 3-oxo-cyclohexyl acetic acid. 2-iso-amyl-2-cyclopentene-1-one is prepared by reacting cyclopentane - 1,2 - dione - isobutyl enol ether with iso amyl magnesium bromide and heating the product with polyphosphonic acid. The n-butyl and n-hexyl compounds may be similarly prepared. The n-hexyl compound may also be prepared by selective chlorination and dehydrochlorination of 2-n-hexyl cyclopentanone. The n-amyl compound may also be prepared by cyclodehydration of g -decalactone. 2-n-butyl-, n-pentyl-, iso-pentyl and n-hexyl-2-cyclohexene-1-ones may be prepared cyclising the corresponding ethyl d -oxoalkanoate according to the Dieckmann method to give the 2-alkyl-cyclohexane-1,3-dione, chlorinating the diketone with PCl3 to give the 2-alkyl-3-chloro-2-cyclohexene-1-one and reducing the latter by means of zinc and potassium iodide. Ethyl d -oxo-9-methyl decanoate (used in the preparation of the isopentyl compound) may be prepared by condensing isohexyl methyl ketone with diethyl carbonate, condensing the resulting ethyl b -oxo-7-methyl octoate with methyl acrylate to give methyl g -carbethoxy-g -oxo-9-methyl decanoate, saponifying and decarboxylating the latter to give d -oxo-9-methyl-decanoic acid and esterifying the acid.ALSO:Perfume compositions comprise as an odour-modifying agent or as an odoriferous ingredient a cycloaliphatic keto ester of the general formula <FORM:0907431/VI/1> wherein R1 represents a methyl or ethyl group, R represents an alkyl radical containing 4-6 carbon atoms and n represents 1 or 2.
GB681461A 1960-02-25 1961-02-24 Improvements in or relating to alicyclic keto-esters and process for their manufacture Expired GB907431A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH212160A CH382731A (en) 1960-02-25 1960-02-25 Process for the preparation of alicyclic keto esters
CH856360A CH490313A (en) 1960-07-27 1960-07-27 Process for preparing ketoesters and use of esters obtained by this process

Publications (1)

Publication Number Publication Date
GB907431A true GB907431A (en) 1962-10-03

Family

ID=25689565

Family Applications (1)

Application Number Title Priority Date Filing Date
GB681461A Expired GB907431A (en) 1960-02-25 1961-02-24 Improvements in or relating to alicyclic keto-esters and process for their manufacture

Country Status (1)

Country Link
GB (1) GB907431A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4537704A (en) * 1983-12-21 1985-08-27 International Flavors & Fragrances Inc. Alkyl substituted and unsubstituted para-carboalkoxy cyclohexanones and organoleptic uses thereof
US4614831A (en) * 1983-12-21 1986-09-30 International Flavors & Fragrances Inc. Process for preparing alkyl substituted para-carboalkoxy cyclohexanones
US4629805A (en) * 1983-12-21 1986-12-16 International Flavors & Fragrances Inc. Alkyl substituted and unsubstituted para-carboalkoxy cyclohexanones and organoleptic uses thereof
US4643903A (en) * 1983-12-21 1987-02-17 International Flavors & Fragrances Inc. Alkyl substituted and unsubstituted para-carboalkoxy cyclohexanones and organoleptic uses thereof
US4668817A (en) * 1983-12-21 1987-05-26 International Flavors & Fragrances Inc. Alkyl substituted para-carboalkoxy cyclohexanones

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4537704A (en) * 1983-12-21 1985-08-27 International Flavors & Fragrances Inc. Alkyl substituted and unsubstituted para-carboalkoxy cyclohexanones and organoleptic uses thereof
US4614831A (en) * 1983-12-21 1986-09-30 International Flavors & Fragrances Inc. Process for preparing alkyl substituted para-carboalkoxy cyclohexanones
US4629805A (en) * 1983-12-21 1986-12-16 International Flavors & Fragrances Inc. Alkyl substituted and unsubstituted para-carboalkoxy cyclohexanones and organoleptic uses thereof
US4643903A (en) * 1983-12-21 1987-02-17 International Flavors & Fragrances Inc. Alkyl substituted and unsubstituted para-carboalkoxy cyclohexanones and organoleptic uses thereof
US4668817A (en) * 1983-12-21 1987-05-26 International Flavors & Fragrances Inc. Alkyl substituted para-carboalkoxy cyclohexanones

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