GB788302A - The manufacture of geranyl-acetone and dihydrogeranyl-acetone and of hexahydro-pseudoionone therefrom - Google Patents

The manufacture of geranyl-acetone and dihydrogeranyl-acetone and of hexahydro-pseudoionone therefrom

Info

Publication number
GB788302A
GB788302A GB4877/55A GB487755A GB788302A GB 788302 A GB788302 A GB 788302A GB 4877/55 A GB4877/55 A GB 4877/55A GB 487755 A GB487755 A GB 487755A GB 788302 A GB788302 A GB 788302A
Authority
GB
United Kingdom
Prior art keywords
geranyl
dihydro
acetone
resulting
hexahydro
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
GB4877/55A
Inventor
George Oswald Chase
Walter Kimel
Joseph Donald Surmatis
Joseph Weber
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.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche AG
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 F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Priority to GB4877/55A priority Critical patent/GB788302A/en
Publication of GB788302A publication Critical patent/GB788302A/en
Expired 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
    • C07C45/62—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
    • 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
    • C07C45/673—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 change of size of the carbon skeleton
    • C07C45/676—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 change of size of the carbon skeleton by elimination of carboxyl groups
    • 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
    • C07B2200/07—Optical isomers

Abstract

Geranyl acetone and dihydro-geranyl acetone respectively are prepared by reacting an acetoacetic alkyl ester with geranyl chloride or bromide or with dihydro geranyl chloride or bromide respectively, in the presence of an alkali metal alkoxide and subjecting the resulting 3-carbalkoxy compound to a ketonic hydrolysis. The methods may be used in a synthesis of hexahydropseudo ionone comprising reacting 6-methyl hepten-5-one-2 or 6-methyl heptanone-2 with an alkali metal derivative of acetylene in liquid ammonia solution and treating the product with an acid, partially hydrogenating the resulting acetylenic carbinol in the presence of a hydrogenation catalyst, e.g. nickel or palladium, which selectively reduces a triple bond to a double bond, reacting the resulting linalool or dihydro linalool with aqueous hydrogen chloride or bromide, converting the so-formed geranyl or dihydrogeranyl halide to geranyl or dihydro geranyl acetone as above described and then catalytically hydrogenating the resulting product as described in Specification 788,301 to hexahydro pseudo-ionone. In examples: (1) linalool prepared as described in Specification 788,301 is reacted at 0 DEG C. with aqueous HCl to form geranyl chloride which is reacted with ethyl aceto acetate in benzene containing sodium methylate as catalyst; the resulting 6 : 10 - dimethyl - 3 - carbethoxyundecadien - 5 : 9 - one - 2 is saponified in aqueous alcoholic KOH and the solution is then acidified and heated to yield geranyl acetone which is catalytically hydrogenated to hexahydro pseudo-ionone as described above; (2) 6-methyl heptanone-2 is converted in like manner via the dihydro geranyl chloride or bromide to dihydro geranyl acetone and thence to hexahydro pseudo ionone. Specification 735,828 also is referred to.
GB4877/55A 1955-02-18 1955-02-18 The manufacture of geranyl-acetone and dihydrogeranyl-acetone and of hexahydro-pseudoionone therefrom Expired GB788302A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB4877/55A GB788302A (en) 1955-02-18 1955-02-18 The manufacture of geranyl-acetone and dihydrogeranyl-acetone and of hexahydro-pseudoionone therefrom

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB4877/55A GB788302A (en) 1955-02-18 1955-02-18 The manufacture of geranyl-acetone and dihydrogeranyl-acetone and of hexahydro-pseudoionone therefrom

Publications (1)

Publication Number Publication Date
GB788302A true GB788302A (en) 1957-12-23

Family

ID=9785514

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4877/55A Expired GB788302A (en) 1955-02-18 1955-02-18 The manufacture of geranyl-acetone and dihydrogeranyl-acetone and of hexahydro-pseudoionone therefrom

Country Status (1)

Country Link
GB (1) GB788302A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3676470A (en) * 1967-05-26 1972-07-11 Toray Industries 1,6-octadiene derivatives and the preparation thereof
US4292454A (en) 1977-12-29 1981-09-29 Scm Corporation Coupling reaction involving a Grignard and allylic halide
EP1256560A2 (en) * 2001-05-11 2002-11-13 Basf Aktiengesellschaft Process for the preparation of higher alpha,beta-unsaturated alcohols

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3676470A (en) * 1967-05-26 1972-07-11 Toray Industries 1,6-octadiene derivatives and the preparation thereof
US4292454A (en) 1977-12-29 1981-09-29 Scm Corporation Coupling reaction involving a Grignard and allylic halide
EP1256560A2 (en) * 2001-05-11 2002-11-13 Basf Aktiengesellschaft Process for the preparation of higher alpha,beta-unsaturated alcohols
EP1256560A3 (en) * 2001-05-11 2003-12-03 Basf Aktiengesellschaft Process for the preparation of higher alpha,beta-unsaturated alcohols
US6828468B2 (en) 2001-05-11 2004-12-07 Basf Aktiengesellschaft Preparation of higher α, β-unsaturated alcohols

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