GB1442536A - Process for the preparation of alpha,ypsilon-diethylenic ketones - Google Patents

Process for the preparation of alpha,ypsilon-diethylenic ketones

Info

Publication number
GB1442536A
GB1442536A GB434074A GB434074A GB1442536A GB 1442536 A GB1442536 A GB 1442536A GB 434074 A GB434074 A GB 434074A GB 434074 A GB434074 A GB 434074A GB 1442536 A GB1442536 A GB 1442536A
Authority
GB
United Kingdom
Prior art keywords
diethylenic
ketones
cis
preparation
pseudoionones
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
GB434074A
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
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 US328558A external-priority patent/US3886217A/en
Priority claimed from US328560A external-priority patent/US3886216A/en
Priority claimed from US328559A external-priority patent/US3886215A/en
Application filed by Rhone Poulenc SA filed Critical Rhone Poulenc SA
Publication of GB1442536A publication Critical patent/GB1442536A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
    • C07C45/513—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an etherified hydroxyl group
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/203—Unsaturated compounds containing keto groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • 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
    • 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)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

1442536 A process for the preparation of α,γ-diethylenic ketones SOC DES USINES CHIMIQUES RHONE-POULENC 30 Jan 1974 [1 Feb 1973 (3)] 04340/74 Heading C2C The invention comprises a process for preparing α,γ-diethylenic ketones which comprises reacting a tertiary acetylenic alcohol with an alk-2-en-2-yl alkyl ether at not more than 150‹ C. in the presence of, as catalyst, cupric sulphate, cupric nitrate or a complex of a metal salt and an amine. The process of the invention is of particular value in the synthesis of cis-#<SP>3</SP>- pseudoionones and cis-#<SP>3</SP>-methyl pseudoionones by reaction of dehydrolinalool or an alkyl or alkenyl homologue thereof with isopropenyl or isobutenyl alkyl ether at about 125‹ C. and the invention also comprises cis-#<SP>3</SP>- trans-#<SP>5</SP>-pseudoionone and its 1-, 3- and 7- methyl homologues. Complexes of pyridine, quinoline, aniline and diethyl, triethyl and n-propylamine with CuSO 4 , CU(NO 3 ) 2 9H 2 O; CuCl 2 , CuSeO 4 , Cu(NO 3 ) 2 3H 2 O, Cu(BF 4 ) 2 and AgNO 3 are prepared by reacting said components in a solvent and optionally adding methanol to precipitate the complex.
GB434074A 1973-02-01 1974-01-30 Process for the preparation of alpha,ypsilon-diethylenic ketones Expired GB1442536A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US328558A US3886217A (en) 1973-02-01 1973-02-01 Process for the preparation of alpha, beta-ethylenic ketones such as delta{hu 3{b -cis-pseudo ionones
US328560A US3886216A (en) 1973-02-01 1973-02-01 Process for the preparation of alfa beta-ethylenic ketones
US328559A US3886215A (en) 1973-02-01 1973-02-01 Process using metal salt-amine complex catalysts for the preparation of alpha beta-ethylenic ketones such as delta-cis-pseudo ionones

Publications (1)

Publication Number Publication Date
GB1442536A true GB1442536A (en) 1976-07-14

Family

ID=27406611

Family Applications (1)

Application Number Title Priority Date Filing Date
GB434074A Expired GB1442536A (en) 1973-02-01 1974-01-30 Process for the preparation of alpha,ypsilon-diethylenic ketones

Country Status (7)

Country Link
JP (1) JPS49109309A (en)
BE (1) BE810466A (en)
CH (1) CH605526A5 (en)
DE (1) DE2404913A1 (en)
FR (1) FR2216257B1 (en)
GB (1) GB1442536A (en)
NL (1) NL7400980A (en)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1273884A (en) * 1959-07-23 1961-10-20 Hoffmann La Roche & Compangnie Process for the preparation of unsaturated ketones

Also Published As

Publication number Publication date
DE2404913A1 (en) 1974-08-15
FR2216257A1 (en) 1974-08-30
BE810466A (en) 1974-07-31
CH605526A5 (en) 1978-09-29
FR2216257B1 (en) 1978-03-24
NL7400980A (en) 1974-08-05
JPS49109309A (en) 1974-10-17

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee