GB922409A - Macrocyclic lactones - Google Patents

Macrocyclic lactones

Info

Publication number
GB922409A
GB922409A GB1262660A GB1262660A GB922409A GB 922409 A GB922409 A GB 922409A GB 1262660 A GB1262660 A GB 1262660A GB 1262660 A GB1262660 A GB 1262660A GB 922409 A GB922409 A GB 922409A
Authority
GB
United Kingdom
Prior art keywords
lactone
ether
ester
yield
general formula
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
GB1262660A
Inventor
Ralph Alexander Raphael
Geoffrey Eglinton
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.)
A Boake Roberts and Co Ltd
Original Assignee
A Boake Roberts and Co Ltd
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 A Boake Roberts and Co Ltd filed Critical A Boake Roberts and Co Ltd
Priority to GB1262660A priority Critical patent/GB922409A/en
Publication of GB922409A publication Critical patent/GB922409A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D315/00—Heterocyclic compounds containing rings having one oxygen atom as the only ring hetero atom according to more than one of groups C07D303/00 - C07D313/00
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0069—Heterocyclic compounds
    • C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms
    • C11B9/0084—Heterocyclic compounds containing only O or S as heteroatoms the hetero rings containing more than six atoms

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

Abstract

Macrocyclic lactones containing 14 to 18 carbon atoms, which are fully saturated or contain one double bond with or without one triple bond, or two double or two triple bonds, are obtained by esterifying an alcohol of general formula HC­C-(CH2)m-OH with a carboxylic acid or acid chloride of general formula HC­C-(CH2)n-CO-X [X=OH or Cl] to form an ester of general formula HC­C-(CH2)m-O-CO-(CH2)n-C­CH in which m and n individually are between 1 and 12, and together total between 9 and 13, then coupling together the terminal acetylenic groups of the resulting ester in the presence of cupric ions (Glaser reaction) with or without submitting the lactone so formed to partial or complete hydrogenation. For the cyclisation step, an ether such as ethyl ether, ethylene glycol dimethyl ether or tetrahydrofuran, and a tertiary base such as pyridine are used, and also an inert waterimmiscible diluent such as benzene. The hydrogenation of the cyclised ester can be carried out stepwise to give ene-yne, diene, monene and saturated lactones. Examples describe the preparation of macrocyclic lactone by reacting but-1-yn-4-ol with undeconoyl chloride in the presence of pyridine and ether, cyclising the resulting ester with the aid of cupric acetate, and then hydrogenating the diynic lactone so formed with Lindlar's catalyst to yield a dienic C15 lactone or with 10% palladium on charcoal to yield monenic C15 lactone or with platinum oxide (PtO2) to yield the saturated lactone cyclopentadecanolide. The lactones may be used in perfumery.
GB1262660A 1960-04-08 1960-04-08 Macrocyclic lactones Expired GB922409A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1262660A GB922409A (en) 1960-04-08 1960-04-08 Macrocyclic lactones

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1262660A GB922409A (en) 1960-04-08 1960-04-08 Macrocyclic lactones

Publications (1)

Publication Number Publication Date
GB922409A true GB922409A (en) 1963-04-03

Family

ID=10008157

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1262660A Expired GB922409A (en) 1960-04-08 1960-04-08 Macrocyclic lactones

Country Status (1)

Country Link
GB (1) GB922409A (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3907831A (en) * 1969-05-29 1975-09-23 Firmenich & Cie Process for preparing lactones
US4490404A (en) * 1983-07-18 1984-12-25 International Flavors & Fragrances Inc. Flavoring with macrocyclic lactone
EP0424787A2 (en) * 1989-10-27 1991-05-02 Firmenich Sa Use of unsaturated macrocyclic ketones as perfuming ingredients
US5266559A (en) * 1989-10-27 1993-11-30 Firmenich S.A. Use of unsaturated macrocyclic lactones as perfuming ingredients
WO1997032948A1 (en) * 1996-03-08 1997-09-12 Firmenich S.A. Fragrant macrocyclic lactones
WO2003038019A1 (en) * 2001-10-26 2003-05-08 Symrise Gmbh & Co. Kg Mixtures for use as musk fragrance

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3907831A (en) * 1969-05-29 1975-09-23 Firmenich & Cie Process for preparing lactones
US4490404A (en) * 1983-07-18 1984-12-25 International Flavors & Fragrances Inc. Flavoring with macrocyclic lactone
EP0424787A2 (en) * 1989-10-27 1991-05-02 Firmenich Sa Use of unsaturated macrocyclic ketones as perfuming ingredients
EP0424787A3 (en) * 1989-10-27 1991-10-23 Firmenich Sa Use of unsaturated macrocyclic ketones as perfuming ingredients
US5266559A (en) * 1989-10-27 1993-11-30 Firmenich S.A. Use of unsaturated macrocyclic lactones as perfuming ingredients
WO1997032948A1 (en) * 1996-03-08 1997-09-12 Firmenich S.A. Fragrant macrocyclic lactones
WO2003038019A1 (en) * 2001-10-26 2003-05-08 Symrise Gmbh & Co. Kg Mixtures for use as musk fragrance
US7767640B2 (en) 2001-10-26 2010-08-03 Symrise Gmbh & Co. Kg Mixtures for use as musk fragrance

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