GB948752A - A process for the manufacture of unsaturated ketones - Google Patents

A process for the manufacture of unsaturated ketones

Info

Publication number
GB948752A
GB948752A GB39314/60A GB3931460A GB948752A GB 948752 A GB948752 A GB 948752A GB 39314/60 A GB39314/60 A GB 39314/60A GB 3931460 A GB3931460 A GB 3931460A GB 948752 A GB948752 A GB 948752A
Authority
GB
United Kingdom
Prior art keywords
methyl
ketene
propionyl
ketones
dehydrolinalool
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
GB39314/60A
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.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche 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 F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of GB948752A publication Critical patent/GB948752A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
    • C11B9/0034—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing six carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
    • C07C403/14—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by doubly-bound oxygen atoms
    • C07C403/16—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by doubly-bound oxygen atoms not being part of —CHO groups
    • 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
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/87—Preparation of ketenes or dimeric ketenes
    • C07C45/89—Preparation of ketenes or dimeric ketenes from carboxylic acids, their anhydrides, esters or halides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/88—Ketenes; Dimeric ketenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/46—Preparation of carboxylic acid esters from ketenes or polyketenes
    • 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
    • C11B9/0007—Aliphatic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)

Abstract

Unsaturated acyclic ketones are prepared by reacting a 1-alkanoyl -1- alkyl ketene containing at least 3 carbon atoms in the alkanoyl group in the presence of a basic catalyst with a tertiary a ,b -unsaturated tertiary alcohol of formula: <FORM:0948752/C2/1> <FORM:0948752/C2/2> wherein R is methyl or a group of formula: <FORM:0948752/C2/3> and hydrolysing the acetoacetate so produced that carbon dioxide is evolved and rearrangement occurs to give ketones of formula: <FORM:0948752/C2/4> <FORM:0948752/C2/5> respectively. Specified basic catalysts are tertiary amines and alkali metal alcoholates, pyridine plus a little acetic acid being preferred. The pyrolysis is preferably carried out between 120-180 DEG C. in the presence of a catalyst e.g. aluminium iso-propylate a promoter e.g. acetic acid and a high boiling solvent e.g. deca- or tetra-hydronaphthalene or diethylene-glycol ethers. The examples describe the preparation of (1) 4,7-dimethyl-octen - 6 - one - 3 from 1-propionyl -1- methyl-ketone and 3-methylbuten -1- ol-3, (2) 8,12-dimethyl -5- ethyltridecatrien-5, 7, 11-one-4 from 1-butyryl-1-ethyl ketene and dehydrolinalool, (3) 4, 7, 11-trimethyl-dodecatrien-4, 6, 10-one- 3 from 1-propionyl-1-methyl ketene and dehydrolinalool, (4) 5-ethyl -8- methyl-nonen -7- one - 4 from 1-butyryl -1- ethyl ketene and 3-methylbuten -3-ol-1, (5) 4, 6, 7-trimethyl-octen -6- one-3 from 1-propionyl -1- methyl ketone and 2, 3-dimethylbuten -1- ol-2 and (6) 5, 6-dimethyl-hepten -5-one-2 and 4, 7, 10, 11-tetramethyl-dodecatrien-4, 6, 10-one-3 from 1-propionyl -1- methyl-ketene and 6-methyl dehydrolinalool. 1-propionyl -1-methyl-ketene and 1-octanoyl -1- hexyl-ketene are prepared from propionyl and octanoyl chloride respectively in the presence of triethylamine under anhydrous conditions. These ketones may be cyclised to give the cyclic unsaturated ketones of Specifications 948,753, 948,754 and 948,755.
GB39314/60A 1959-11-16 1960-11-16 A process for the manufacture of unsaturated ketones Expired GB948752A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US85297359A 1959-11-16 1959-11-16

Publications (1)

Publication Number Publication Date
GB948752A true GB948752A (en) 1964-02-05

Family

ID=25314689

Family Applications (4)

Application Number Title Priority Date Filing Date
GB46764/62A Expired GB948753A (en) 1959-11-16 1960-11-16 Unsaturated cyclic ketones
GB27472/63A Expired GB948755A (en) 1959-11-16 1960-11-16 Unsaturated ketones
GB46765/62A Expired GB948754A (en) 1959-11-16 1960-11-16 The manufacture of unsaturated cyclic ketones
GB39314/60A Expired GB948752A (en) 1959-11-16 1960-11-16 A process for the manufacture of unsaturated ketones

Family Applications Before (3)

Application Number Title Priority Date Filing Date
GB46764/62A Expired GB948753A (en) 1959-11-16 1960-11-16 Unsaturated cyclic ketones
GB27472/63A Expired GB948755A (en) 1959-11-16 1960-11-16 Unsaturated ketones
GB46765/62A Expired GB948754A (en) 1959-11-16 1960-11-16 The manufacture of unsaturated cyclic ketones

Country Status (5)

Country Link
BE (1) BE596886A (en)
CH (1) CH397645A (en)
DE (1) DE1181354B (en)
GB (4) GB948753A (en)
NL (1) NL257967A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB201208566D0 (en) * 2012-05-16 2012-06-27 Givaudan Sa Organic compounds

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE960845C (en) * 1954-09-27 1957-03-28 Givaudan & Cie Sa Perfume

Also Published As

Publication number Publication date
DE1181354B (en) 1964-11-12
GB948755A (en) 1964-02-05
CH397645A (en) 1965-08-31
GB948754A (en) 1964-02-05
NL257967A (en)
GB948753A (en) 1964-02-05
BE596886A (en) 1961-05-09

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