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FR2302989A1 - PROCESS FOR PREPARING STEREOSPECIFIC ISOMERS OF NEROLIDOL - Google Patents

PROCESS FOR PREPARING STEREOSPECIFIC ISOMERS OF NEROLIDOL

Info

Publication number
FR2302989A1
FR2302989A1 FR7614800A FR7614800A FR2302989A1 FR 2302989 A1 FR2302989 A1 FR 2302989A1 FR 7614800 A FR7614800 A FR 7614800A FR 7614800 A FR7614800 A FR 7614800A FR 2302989 A1 FR2302989 A1 FR 2302989A1
Authority
FR
France
Prior art keywords
delta4
cis
isomers
iii
trans
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
FR7614800A
Other languages
French (fr)
Other versions
FR2302989B1 (en
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.)
Kuraray Co Ltd
Original Assignee
Kuraray 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
Priority claimed from JP49119797A external-priority patent/JPS5148604A/en
Priority claimed from JP49119798A external-priority patent/JPS593452B2/en
Application filed by Kuraray Co Ltd filed Critical Kuraray Co Ltd
Publication of FR2302989A1 publication Critical patent/FR2302989A1/en
Application granted granted Critical
Publication of FR2302989B1 publication Critical patent/FR2302989B1/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
    • C07C45/61—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
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
    • C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
    • C07C29/42—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones with compounds containing triple carbon-to-carbon bonds, e.g. with metal-alkynes
    • 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
    • C07C45/70—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 by reaction with functional groups containing oxygen only in singly bound form
    • C07C45/71—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 by reaction with functional groups containing oxygen only in singly bound form being hydroxy 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
    • C07C45/78—Separation; Purification; Stabilisation; Use of additives
    • C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
    • C07C45/82—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/27—Preparation of carboxylic acid esters from ortho-esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/48—Separation; Purification; Stabilisation; Use of additives
    • C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
    • C07C67/54—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/09—Geometrical isomers

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Fats And Perfumes (AREA)

Abstract

Process for prepg. specific stereoisomers of farnesylacetic aced or its esters of formula (I): CH3. C(CH3)=CH.CH2CH2. C(CH3)DELTA8=CH. CH2CH2. C(CH3)DELTA4= CHCH2CH2COOR2 (I) (R2 = H, 1-6C alkyl, 3-6C cycloalkyl, 2-6C alkenyl or 3-6C cycloalkenyl)comprises rectifying a mixt. of (i) DELTA4,8-cis and DELTA4-trans-DELTA-cis (I); (ii) DELTA4,8-trans (I) or (III) all 4 isomers to recovery from mixts. (i) and (ii) both components and from (iii) the DELTA4,8-cis isomers. Similar processes for separg. DELTA6-cis and DELTA6-trans isomers of nerolidol (II) and DELTA5-cis and DELTA5-trans geranylacetone (III) are also new. (I) are anti-ulcer agents (for which purpose individual isomers are pref), perfumes and aroma agents. (II) and (III) are intermediates for (I), perfumes and cpds. with juvenile hormone activity; (II) is also used to make isophytol a starting material for Vitamin E. Recovery of individual isomers is almost quantitative.
FR7614800A 1974-10-17 1976-05-17 PROCESS FOR PREPARING STEREOSPECIFIC ISOMERS OF NEROLIDOL Granted FR2302989A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP49119797A JPS5148604A (en) 1974-10-17 1974-10-17 Ritsutaikisei sareta neroridooruno seizoho
JP49119798A JPS593452B2 (en) 1974-10-17 1974-10-17 Method for producing sterically regulated nerolidol

Publications (2)

Publication Number Publication Date
FR2302989A1 true FR2302989A1 (en) 1976-10-01
FR2302989B1 FR2302989B1 (en) 1979-07-27

Family

ID=26457467

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7614800A Granted FR2302989A1 (en) 1974-10-17 1976-05-17 PROCESS FOR PREPARING STEREOSPECIFIC ISOMERS OF NEROLIDOL

Country Status (1)

Country Link
FR (1) FR2302989A1 (en)

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS VOL. 69, NO. 77526H MASAHARU ET AL. *
CHEMICAL ABSTRACTS VOL. 85, NO. 177700J CITANT JA - A 76 29 401 KURARAY PUBLIE LE 12 MARS 1976) *
HELVETICA CHIMICA ACTA VOL. 42, FASCICULE 7, 01-12-1959, BASEL. A. OFNER ET AL.: "276-SYNTHETISCHES NEROLIDOL UND VERWANDTE C15 ALKOHOLE" PAGES 2577-2584 *

Also Published As

Publication number Publication date
FR2302989B1 (en) 1979-07-27

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