[go: up one dir, main page]

FR2312484A1 - Oppenauer oxidn. of allyl and benzyl alcohols - using furfural as hydrogen acceptor - Google Patents

Oppenauer oxidn. of allyl and benzyl alcohols - using furfural as hydrogen acceptor

Info

Publication number
FR2312484A1
FR2312484A1 FR7539718A FR7539718A FR2312484A1 FR 2312484 A1 FR2312484 A1 FR 2312484A1 FR 7539718 A FR7539718 A FR 7539718A FR 7539718 A FR7539718 A FR 7539718A FR 2312484 A1 FR2312484 A1 FR 2312484A1
Authority
FR
France
Prior art keywords
oppenauer
furfural
prod
oxidn
allyl
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.)
Granted
Application number
FR7539718A
Other languages
French (fr)
Other versions
FR2312484B1 (en
Inventor
William Jarold Ehmann
Walter Earl Johnson Jr
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.)
SCM Corp
Original Assignee
SCM Corp
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 US05/582,114 external-priority patent/US4055601A/en
Application filed by SCM Corp filed Critical SCM Corp
Publication of FR2312484A1 publication Critical patent/FR2312484A1/en
Application granted granted Critical
Publication of FR2312484B1 publication Critical patent/FR2312484B1/fr
Granted legal-status Critical Current

Links

Classifications

    • 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
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
    • C07C45/37—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of >C—O—functional groups to >C=O 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
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Furan Compounds (AREA)

Abstract

The Oppenauer oxidn. of (a) primary allyl alcohols which are 2-substd. by a hydrocarbyl gp. and in which the allylic double bond is non-cyclic, exocyclic or endocyclic, (b) primary benzyl alcohols and (c) 3,3-disubstd. allyl alcohols, is carried out in the presence of an Oppenauer catalyst and furfural as H acceptor, to give the corresp. aldehyde as prod. and furfuryl alcohol as by-prod. The process is esp. useful for oxidising geraniol and nerol to citral, which is useful as a synthetic flavour and perfume and as an inter. for pseudoionone, which in turn is an intermediate for vitamin E and for alpha-and beta-ionone (vitamin A inters.). The use of furfural as H acceptor eliminates the aldol condensation side-reaction association with the use of acetone, and gives high yields (e.g., 94-100% for citral); furfuryl alcohol is a valuable by-prod.
FR7539718A 1975-05-30 1975-12-24 Oppenauer oxidn. of allyl and benzyl alcohols - using furfural as hydrogen acceptor Granted FR2312484A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US58211375A 1975-05-30 1975-05-30
US05/582,114 US4055601A (en) 1974-01-28 1975-05-30 Process for the oxidation of primary allylic alcohols

Publications (2)

Publication Number Publication Date
FR2312484A1 true FR2312484A1 (en) 1976-12-24
FR2312484B1 FR2312484B1 (en) 1980-09-19

Family

ID=27078498

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7539718A Granted FR2312484A1 (en) 1975-05-30 1975-12-24 Oppenauer oxidn. of allyl and benzyl alcohols - using furfural as hydrogen acceptor

Country Status (5)

Country Link
JP (1) JPS51141801A (en)
CH (1) CH605514A5 (en)
DE (1) DE2556161A1 (en)
FR (1) FR2312484A1 (en)
NL (1) NL7514890A (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH07103095B2 (en) * 1990-01-08 1995-11-08 株式会社クラレ Method for producing vitamin A aldehyde
US6703527B2 (en) 2001-05-24 2004-03-09 Nikken Chemicals Co., Ltd. Method for oxidation of allyl alcohol
ITMI20051431A1 (en) * 2005-07-25 2007-01-26 Endura Spa PROCESS FOR THE PREPARATION OF AROMATIC ALDEHIDES 3,4-DIOSSO-SUBSTITUTE
CN108409560B (en) * 2018-04-11 2021-04-06 合肥利夫生物科技有限公司 1, 13-tridecanediol ester and preparation method of 1, 13-tridecanediol thereof

Also Published As

Publication number Publication date
CH605514A5 (en) 1978-09-29
NL7514890A (en) 1976-12-02
JPS51141801A (en) 1976-12-07
DE2556161A1 (en) 1976-12-16
FR2312484B1 (en) 1980-09-19

Similar Documents

Publication Publication Date Title
US4052341A (en) 3-methyl-5-(2,2,3-trimethylcyclopent-3-en-1-yl)pentan-2-ol compound and perfume compositions
TW241285B (en)
US4252986A (en) Fixative for perfume compositions
GB1205048A (en) Cyclopentadecenones
DE69729809T2 (en) Cyclopentanbutanolderivate
US3514489A (en) Sec-butyl cyclohexane carboxaldenhydes
FR2312484A1 (en) Oppenauer oxidn. of allyl and benzyl alcohols - using furfural as hydrogen acceptor
US4311718A (en) Flavoring with 2,4,4-trimethyl-3-(buta-1,3-dienyl)cyclohex-2-en-one
Thomas et al. 10-Epijunenol, a new cis-eudesmane sesquiterpenoid
CH633508A5 (en) METHOD FOR PRODUCING NEW CYCLOALIPHATIC SATURED AND UNSATURATED KETONES USED AS AROMA AND FRAGRANCES.
Rowland et al. Macrocyclic Diterpenes Isolated from Tobacco. α-and β-3, 8, 13-Duvatriene-1, 5-diols
US4128729A (en) Bicyclo[2.2.2]-octene derivatives and mixtures thereof
JPH0513135B2 (en)
DE3071409D1 (en) Furyl intermediates of cardenolides, their synthesis and production of cardenolides and their isomers therefrom
Andersen et al. A New Total Synthesis of Bulnesol
Moyer et al. An improved synthesis of peroxybenzoic acid
JPS5940154B2 (en) Theaspiran manufacturing method
ES355013A1 (en) 4-Methyl-8-vinyl-4,7- and -4,8-nonadienals
BAUMANN et al. Alk-1-enyl ethers of glycerol and ethanediol
US4072719A (en) 4-(2,6,6-Trimethyl-2-cyclohexen-1-ylidene)-butan-2-ol
DE4212941A1 (en) Penten derivatives, their preparation and use
Sasaki A modified Wittig synthesis of 6, 10-dimethyl-3, 9-undecadien-2-one, ethyl 5, 9-dimethyl-2, 8-decadienonate, and their α-alkyl homologs: stereochemistry of the reaction and conformation of the products
JPS601119A (en) Fragrant composition
GB1379014A (en) Azulene derivatives
Buttery et al. Volatile hop constituents: Characterisation of β‐copaene and pentadec‐6‐ene‐2‐one

Legal Events

Date Code Title Description
ST Notification of lapse