GB1087837A

GB1087837A – Improvements in and relating to process of preparing isophytol
– Google Patents

GB1087837A – Improvements in and relating to process of preparing isophytol
– Google Patents
Improvements in and relating to process of preparing isophytol

Info

Publication number
GB1087837A

GB1087837A
GB36633/65A
GB3663365A
GB1087837A
GB 1087837 A
GB1087837 A
GB 1087837A
GB 36633/65 A
GB36633/65 A
GB 36633/65A
GB 3663365 A
GB3663365 A
GB 3663365A
GB 1087837 A
GB1087837 A
GB 1087837A
Authority
GB
United Kingdom
Prior art keywords
pseudo
acetal
phyton
give
pict
Prior art date
1964-09-03
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
GB36633/65A
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.)

Adisseo France SAS

Original Assignee
AEC Societe de Chimie Organique and Biologique 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.)
1964-09-03
Filing date
1965-08-26
Publication date
1967-10-18

1965-08-26
Application filed by AEC Societe de Chimie Organique and Biologique SA
filed
Critical
AEC Societe de Chimie Organique and Biologique SA

1967-10-18
Publication of GB1087837A
publication
Critical
patent/GB1087837A/en

Status
Expired
legal-status
Critical
Current

Links

Espacenet

Global Dossier

Discuss

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

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

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

C07C45/51—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

C07C45/515—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 acetalised, ketalised hemi-acetalised, or hemi-ketalised 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

C07C45/62—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 hydrogenation of carbon-to-carbon double or triple bonds

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

C07C45/61—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

C07C45/72—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 of compounds containing >C = O groups with the same or other compounds containing >C = O groups

C07C45/74—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 of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration

Abstract

Isophytol, which has the formula is prepared by condensing phyton, which has the formula with a Grignard reagent where X is halogen and both Y’s are hydrogen atoms or free valencies united so that the carbon atoms are joined by an acetylenic bond, hydrolysing the resulting addition compound and, when Y is not hydrogen, subjecting acetylenic alcohol to partial catalytic hydrogenation. The starting material, phyton, may be made according to the reaction scheme shown in Fig. 2. Citral (II) is condensed with an acetal of b -ketobutyraldehyd where R is a C1- 6 alkyl group, to give the C14-pseudo acetal VI which reacted with a Grignard reagent CH3MgX (X is halogen) and the resultant organometallic compound hydrolysed to the C15-pseudo-hydroxy acetal (VII) which on acid hydrolysis in acetone yields the C15-pseudo-aldehyde (VIII). This aldehyde is condensed with acetone to give the C18-pseudo-ketone (IX) which on catalytic hydrogenation yields phyton. The C14-pseudo-acetal (VI) may also be prepared by formylating pseudo-ionone (III) by Claisen’s method to give the enolate V which is acetalized with an alcohol ROH to yield (VI). In the example some of the intermediates are characterized as the semicarbazones.

GB36633/65A
1964-09-03
1965-08-26
Improvements in and relating to process of preparing isophytol

Expired

GB1087837A
(en)

Applications Claiming Priority (1)

Application Number
Priority Date
Filing Date
Title

FR986994A

FR1460512A
(en)

1964-09-03
1964-09-03

Isophytol preparation process

Publications (1)

Publication Number
Publication Date

GB1087837A
true

GB1087837A
(en)

1967-10-18

Family
ID=8837696
Family Applications (1)

Application Number
Title
Priority Date
Filing Date

GB36633/65A
Expired

GB1087837A
(en)

1964-09-03
1965-08-26
Improvements in and relating to process of preparing isophytol

Country Status (4)

Country
Link

CH
(2)

CH445472A
(en)

DE
(1)

DE1298973B
(en)

FR
(1)

FR1460512A
(en)

GB
(1)

GB1087837A
(en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

US4292454A
(en)

1977-12-29
1981-09-29
Scm Corporation
Coupling reaction involving a Grignard and allylic halide

1964

1964-09-03
FR
FR986994A
patent/FR1460512A/en
not_active
Expired

1965

1965-08-17
CH
CH1152265A
patent/CH445472A/en
unknown

1965-08-17
CH
CH1388667A
patent/CH458316A/en
unknown

1965-08-26
GB
GB36633/65A
patent/GB1087837A/en
not_active
Expired

1965-09-01
DE
DEA50157A
patent/DE1298973B/en
active
Pending

Also Published As

Publication number
Publication date

CH445472A
(en)

1967-10-31

DE1298973B
(en)

1969-07-10

FR1460512A
(en)

1966-01-07

CH458316A
(en)

1968-06-30

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