FR2302992A1 - Prepn. of individual farnesylacetic acid (esters) geometric isomers - by rectification of isomer mixts. obtd. from nerolidol - Google Patents

Prepn. of individual farnesylacetic acid (esters) geometric isomers - by rectification of isomer mixts. obtd. from nerolidol

Info

Publication number
FR2302992A1
FR2302992A1 FR7614799A FR7614799A FR2302992A1 FR 2302992 A1 FR2302992 A1 FR 2302992A1 FR 7614799 A FR7614799 A FR 7614799A FR 7614799 A FR7614799 A FR 7614799A FR 2302992 A1 FR2302992 A1 FR 2302992A1
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
FR7614799A
Other languages
French (fr)
Other versions
FR2302992B3 (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
Application filed by Kuraray Co Ltd filed Critical Kuraray Co Ltd
Publication of FR2302992A1 publication Critical patent/FR2302992A1/en
Application granted granted Critical
Publication of FR2302992B3 publication Critical patent/FR2302992B3/fr
Granted legal-status Critical Current

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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
    • C07C45/78—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
    • 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.
FR7614799A 1974-09-10 1976-05-17 Prepn. of individual farnesylacetic acid (esters) geometric isomers - by rectification of isomer mixts. obtd. from nerolidol Granted FR2302992A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP49104062A JPS5132511A (en) 1974-09-10 1974-09-10 Ritsutaikiseisareta geraniruaseton no seizohoho

Publications (2)

Publication Number Publication Date
FR2302992A1 true FR2302992A1 (en) 1976-10-01
FR2302992B3 FR2302992B3 (en) 1980-10-24

Family

ID=14370676

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7614799A Granted FR2302992A1 (en) 1974-09-10 1976-05-17 Prepn. of individual farnesylacetic acid (esters) geometric isomers - by rectification of isomer mixts. obtd. from nerolidol

Country Status (2)

Country Link
JP (1) JPS5132511A (en)
FR (1) FR2302992A1 (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014096067A1 (en) * 2012-12-18 2014-06-26 Dsm Ip Assets B.V. (6r,10r)-6,10,14-trimetylpentadecan-2-one prepared from (r)-6,10,14-trimetylpentadec-5-en-2-one
WO2014096098A1 (en) * 2012-12-18 2014-06-26 Dsm Ip Assets B.V. (6r,10r)-6,10,14-trimetylpentadecan-2-one prepared from 6,10,14-trimetylpentadeca-5,9,13-trien-2-one or 6,10,14-trimetylpentadeca-5,9-dien-2-one

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5578576A (en) * 1978-12-08 1980-06-13 Nec Corp Semiconductor device
CN110563566A (en) * 2012-12-18 2019-12-13 帝斯曼知识产权资产管理有限公司 Nitric oxide as a catalyst for cis/trans isomerization of unsaturated compounds
CN104884419B (en) * 2012-12-18 2018-03-23 帝斯曼知识产权资产管理有限公司 Cis/trans isomerization catalyst of the polymercaptan as unsaturated compound

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014096067A1 (en) * 2012-12-18 2014-06-26 Dsm Ip Assets B.V. (6r,10r)-6,10,14-trimetylpentadecan-2-one prepared from (r)-6,10,14-trimetylpentadec-5-en-2-one
WO2014096098A1 (en) * 2012-12-18 2014-06-26 Dsm Ip Assets B.V. (6r,10r)-6,10,14-trimetylpentadecan-2-one prepared from 6,10,14-trimetylpentadeca-5,9,13-trien-2-one or 6,10,14-trimetylpentadeca-5,9-dien-2-one
US9611200B2 (en) 2012-12-18 2017-04-04 Dsm Ip Assets B.V. (6R,10R)-6,10,14-trimetylpentadecan-2-one prepared from 6,10,14 trimetylpentadeca-5,9,13-trien-2-one or 6,10,14-trimetylpentadeca-5,9-dien-2-one
EA033302B1 (en) * 2012-12-18 2019-09-30 ДСМ АйПи АССЕТС Б.В. (6r,10r)-6,10,14-trimetylpentadecan-2-one prepared from 6,10,14-trimetylpentadeca-5,9,13-trien-2-one or 6,10,14-trimetylpentadeca-5,9-dien-2-one
EA033302B9 (en) * 2012-12-18 2020-01-22 ДСМ АйПи АССЕТС Б.В. (6r,10r)-6,10,14-trimetylpentadecan-2-one prepared from 6,10,14-trimetylpentadeca-5,9,13-trien-2-one or 6,10,14-trimetylpentadeca-5,9-dien-2-one

Also Published As

Publication number Publication date
JPS5132511A (en) 1976-03-19
FR2302992B3 (en) 1980-10-24

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