WO2006079608A3 - Method for producing 2-oxo-cycloalkane carboxylic acid ethyl esters and 2-oxo-cycloalkene carboxylic acid ethyl esters - Google Patents

Method for producing 2-oxo-cycloalkane carboxylic acid ethyl esters and 2-oxo-cycloalkene carboxylic acid ethyl esters Download PDF

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Publication number
WO2006079608A3
WO2006079608A3 PCT/EP2006/050343 EP2006050343W WO2006079608A3 WO 2006079608 A3 WO2006079608 A3 WO 2006079608A3 EP 2006050343 W EP2006050343 W EP 2006050343W WO 2006079608 A3 WO2006079608 A3 WO 2006079608A3
Authority
WO
WIPO (PCT)
Prior art keywords
oxo
carboxylic acid
acid ethyl
ethyl esters
cycloalkane
Prior art date
Application number
PCT/EP2006/050343
Other languages
German (de)
French (fr)
Other versions
WO2006079608A2 (en
Inventor
Aurelia Reckziegel
Original Assignee
Symrise Gmbh & Co Kg
Aurelia Reckziegel
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 Symrise Gmbh & Co Kg, Aurelia Reckziegel filed Critical Symrise Gmbh & Co Kg
Publication of WO2006079608A2 publication Critical patent/WO2006079608A2/en
Publication of WO2006079608A3 publication Critical patent/WO2006079608A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/385—Saturated compounds containing a keto group being part of a ring
    • 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
    • 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
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • 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

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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 relates to a method for producing a 2-oxo-cycloalkane- or 2-oxo-cycloalkene carboxylic acid ethyl ester of formula (I). According to said method, a diazo ethyl acetate is reacted with a cycloalkanone or cycloalkenone of formula (II), in which X represents a saturated or mono or polyunsaturated C9-C19 chain that is optionally substituted by a C1-C4 alkyl group, in the presence of a Lewis acid to form the 2-oxo-cycloalkane- or 2-oxo-cycloalkene carboxylic acid ethyl ester formula (I). The molar quantity of Lewis acid that is introduced ranges between 0.01 and 0.5 equivalents, in relation to the quantity of cycloalkanone or cycloalkenone of formula (II).
PCT/EP2006/050343 2005-01-25 2006-01-20 Method for producing 2-oxo-cycloalkane carboxylic acid ethyl esters and 2-oxo-cycloalkene carboxylic acid ethyl esters WO2006079608A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE200510003338 DE102005003338A1 (en) 2005-01-25 2005-01-25 Preparation of 2-oxo-cyclo-alkane/alkene carboxylic acid ethylesters, useful as intermediate products to prepare macrocyclic ketones, comprises reacting diazoacetic acid ethylester with cyclo-alkanone/alkenone in the presence of Lewis acid
DE102005003338.5 2005-01-25

Publications (2)

Publication Number Publication Date
WO2006079608A2 WO2006079608A2 (en) 2006-08-03
WO2006079608A3 true WO2006079608A3 (en) 2006-11-02

Family

ID=36613427

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2006/050343 WO2006079608A2 (en) 2005-01-25 2006-01-20 Method for producing 2-oxo-cycloalkane carboxylic acid ethyl esters and 2-oxo-cycloalkene carboxylic acid ethyl esters

Country Status (2)

Country Link
DE (1) DE102005003338A1 (en)
WO (1) WO2006079608A2 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7838487B2 (en) * 2007-01-16 2010-11-23 International Flavors & Fragrances Inc. Macrocyclic musk

Non-Patent Citations (8)

* Cited by examiner, † Cited by third party
Title
BOIVIN J ET AL: "An Efficient Synthesis of Large Ring Acetylenes", TETRAHEDRON LETTERS, vol. 36, no. 32, 7 August 1995 (1995-08-07), pages 5737 - 5740, XP004027592, ISSN: 0040-4039 *
BRUHN J ET AL: "DIE COPE-UMLAGERUNG ALS PRINZIP EINER REPETIERBAREN RINGERWEITERUNG THE COPE REARRANGEMENT, A REACTION FOR REPEATABLE RING EXPANSION", HELVETICA CHIMICA ACTA, vol. 62, no. 8, 1979, pages 2630 - 2654, XP009068987, ISSN: 0018-019X *
H. J. LIU AND T. OGINO: "A NEW APPROACH TO THE SYNTHESIS OF HYDRINDANONECARBOXYLATES", TETRAHEDRON LETTERS, vol. 49, 1973, pages 4937 - 4940, XP002392901 *
JAMES A. MARSHALL AND VICKI H. AUDIA: "THE STEREOCHEMISTRY OF SN2' ADDITION TO MACROCYCLIC ALPHA- METHYLENECYCLOALKYLIDENE EPOXIDES BY ORGANOCOPPER REAGENTS", J. ORG. CHEM., vol. 52, 1987, pages 1106 - 1113, XP002392899 *
KARPF M ET AL: "ANWENDUNG VON RINGERWEITERUNGEN ZUR HERSTELLUNG VON RAC-MUSCON UND EXALTON APPLICATION OF RING EXPANSIONS FOR THE PREPARATION OF RAC-MUSCONE AND EXALTONE", HELVETICA CHIMICA ACTA, vol. 58, no. 8, 1975, pages 2409 - 2422, XP009068986, ISSN: 0018-019X *
VINOD DAVE AND E. W. WARNHOFF: "REGIOSPECIFIC HOMOLOGATION OF UNSYMMETRICAL KETONES", J.ORG.CHEM., vol. 48, 1983, pages 2590 - 2598, XP002392900 *
WILLIAM L. MOCK AND MARVIS E. HARTMAN: "MECHANISM OF THE TRIETHYLOXONIUM ION CATALYSED HOMOLOGATION OF KETONES WITH DIAZOACETIC ESTERS", J.ORG.CHEM., vol. 42, no. 3, 1977, pages 466 - 472, XP002392902 *
WILLIAM L. MOCK AND MARVIS E. HARTMAN: "SYNTHETIC SCOPE OF THE TRIETHYLOXONIUM ION CATALYZED HOMOLOGATION OF KETONES WITH DIAZOACETIC ESTERS", J.ORG.CHEM., vol. 42, no. 3, 1977, pages 459 - 465, XP002392903 *

Also Published As

Publication number Publication date
WO2006079608A2 (en) 2006-08-03
DE102005003338A1 (en) 2006-07-27

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