GB1059839A - Process for preparing ketones and novel ketones so prepared - Google Patents

Process for preparing ketones and novel ketones so prepared

Info

Publication number
GB1059839A
GB1059839A GB4708163A GB4708163A GB1059839A GB 1059839 A GB1059839 A GB 1059839A GB 4708163 A GB4708163 A GB 4708163A GB 4708163 A GB4708163 A GB 4708163A GB 1059839 A GB1059839 A GB 1059839A
Authority
GB
United Kingdom
Prior art keywords
alkyl
alkenyl
ketones
methyl
salts
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
GB4708163A
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.)
Rhone Poulenc SA
Original Assignee
Rhone Poulenc SA
Societe des Usines Chimiques Rhone Poulenc SA
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 Rhone Poulenc SA, Societe des Usines Chimiques Rhone Poulenc SA filed Critical Rhone Poulenc SA
Publication of GB1059839A publication Critical patent/GB1059839A/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
    • 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
    • C07C45/68—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 increase in the number of carbon atoms
    • 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
    • C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom

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)
  • Fats And Perfumes (AREA)

Abstract

Substituted ketones are prepared by reacting a ketone containing a > CH-CO-group with an organic halide in which the halogen atom is not deactivated by attachment to an aryl nucleus or vinyl group in the presence of (1) sodium or potassium hydroxide and (2) an amine catalyst selected from inorganic nitrogen bases and their salts, primary, secondary, tertiary and quaternary aliphatic, cyclo-aliphatic and araliphatic amines, saturated mononuclear heterocyclic amines containing 5 or 6 ring atoms, 1 or 2 of said atoms being N1 or 1 N and 10, the remainder being C1 and salts of such amines (including amino acids and basic ion-exchange resins containing amino groups and their salts) and amides (including urea). Temperatures of -20 DEG to +150 DEG C. may be used. An inert organic solvent may be present. Specified suitable halides include alkyl, alkenyl, alkynyl, cycloaliphatic and aralkyl chlorides, bromides and iodides. Specified ketones include alkyl, olefinic, alicyclic and aryl ketones. The invention also comprises unsaturated ketones of formula <FORM:1059839/C2/1> where R and R3 are each C1- 6 alkyl or C2- 6 alkenyl, and R1 and R2 are each H, C1- 6 alkyl or C2- 6 alkenyl, or R1 and R2 together are C2- 6 alkylidene, and R1 and R3 together may be a trimethylene chain, with the proviso that where R1 and R2 are both H, R3 contains at least 3 C, and that where R2 is H and R1 is other than H and not linked to R3, either R3 is Me or Et and R1 is C3- 6 alkyl or C4- 6 alkenyl, or R is 4-methyl3-pentenyl, or R3 contains at least 4 C.ALSO:Perfume compositions comprise one or more unsaturated ketones of formula <FORM:1059839/A5-A6/1> where R and R3 are each C1-6 alkyl or C2-6 alkenyl and R1 and R2 are each H C1-6 alkyl or C2-6 alkenyl, or R1 and R2 together are C2-6 alkylidene, and R1 and R3 together may be a trimethylene chain, with the proviso that where R1 and R2 are both H, R3 contains at least 3C, and that where R2 is H and R1 is other than H and not linked to R3, either R3 is Me or Et and R1 is C3-6 alkyl or C4-6 alkenyl or R is 4-methyl-3-pentenyl, or R3 contains at least 4C, optionally in association with a conventional diluent and/or other odoriferous principles. A synthetic lavender composition comprises linalyl acetate, linalool, coumarin, 4,7-dimethyl-6-octen-3-one, 8-methyl-7-nonen-4-one, 6-methyl-3-ethyl-5-hepten-2-one and 2-(3-methyl -2-butenyl)-cyclopentanone.
GB4708163A 1962-11-29 1963-11-28 Process for preparing ketones and novel ketones so prepared Expired GB1059839A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US24103662A 1962-11-29 1962-11-29

Publications (1)

Publication Number Publication Date
GB1059839A true GB1059839A (en) 1967-02-22

Family

ID=22908979

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4708163A Expired GB1059839A (en) 1962-11-29 1963-11-28 Process for preparing ketones and novel ketones so prepared

Country Status (3)

Country Link
CH (1) CH419085A (en)
GB (1) GB1059839A (en)
NL (1) NL150095B (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4045489A (en) * 1976-01-15 1977-08-30 International Flavors & Fragrances Inc. Process for producing cis-jasmone
US4117015A (en) * 1976-08-11 1978-09-26 International Flavors & Fragrances Inc. 1-acetyl-3-3-dimethyl-(2-propenyl)cyclohexane, process for producing same and organoleptic uses of same
EP0141569A2 (en) * 1983-10-25 1985-05-15 BUSH BOAKE ALLEN Limited Perfumery compounds and their preparation

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4045489A (en) * 1976-01-15 1977-08-30 International Flavors & Fragrances Inc. Process for producing cis-jasmone
US4117015A (en) * 1976-08-11 1978-09-26 International Flavors & Fragrances Inc. 1-acetyl-3-3-dimethyl-(2-propenyl)cyclohexane, process for producing same and organoleptic uses of same
EP0141569A2 (en) * 1983-10-25 1985-05-15 BUSH BOAKE ALLEN Limited Perfumery compounds and their preparation
EP0141569A3 (en) * 1983-10-25 1985-08-14 Bush Boake Allen Limited Perfumery compounds and their preparation

Also Published As

Publication number Publication date
NL150095B (en) 1976-07-15
CH419085A (en) 1966-08-31

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