GB1101624A - A process for the manufacture of acetylenic carbinols - Google Patents

A process for the manufacture of acetylenic carbinols

Info

Publication number
GB1101624A
GB1101624A GB2247/66A GB224766A GB1101624A GB 1101624 A GB1101624 A GB 1101624A GB 2247/66 A GB2247/66 A GB 2247/66A GB 224766 A GB224766 A GB 224766A GB 1101624 A GB1101624 A GB 1101624A
Authority
GB
United Kingdom
Prior art keywords
formula
alkali metal
acetylene compound
alkyl
reaction
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
GB2247/66A
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
Publication of GB1101624A publication Critical patent/GB1101624A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C35/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic
    • C07C35/06—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic containing a five-membered rings
    • 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
    • C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C35/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic
    • C07C35/04—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic containing a three or four-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C35/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic
    • C07C35/04—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic containing a three or four-membered rings
    • C07C35/045—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic containing a three or four-membered rings containing a four-membered ring

Abstract

Acetylenic carbinols of the Formula I <FORM:1101624/C2/1> where R represents a C1- 7 alkyl, C2- 7 alkenyl, C2- 7 alkynyl, phenyl or C1- 7 alkyl substituted phenyl group R1 represents a C1- 7 alkyl, C2- 7 alkenyl or C2- 7 alkynyl group, R2 represents a C1- 18 hydrocarbon group or R1 and R2 together with the carbon to which they are attached form a cycloalkyl or cycloalkenyl ring containing up to 7 carbon atoms, are prepared by reacting an acetylene compound of the formula HC­C-[H or R] with a ketone of the formula <FORM:1101624/C2/2> in the liquid phase at a temperature above about - 10 DEG C. and a pressure greater than about 34 atmospheres in liquid ammonia in the presence of a catalytic amount of an alkali metal acetylide or an alkali metal derivative of the acetylenic carbinol of the Formula I, the acetylene compound, the ketone and the catalyst being dissolved in the liquid ammonia throughout the reaction. The liquid phase is defined as being devoid of any vapour phase or solids. It is preferred to effect the reaction in a pipe reactor. It is preferred to operate at - 10 DEG to 50 DEG C. and 34-136 atms. The catalyst may be formed in situ by addition of an alkali metal or an alkali metal amide to the reaction mixture containing the acetylene compound starting material. Examples relate to the preparation of 3-methyl-butyn-1-ol-3, dehydrolinalool, dehydronerolidol and dehydroisophytol.
GB2247/66A 1965-01-25 1966-01-18 A process for the manufacture of acetylenic carbinols Expired GB1101624A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US42793565A 1965-01-25 1965-01-25

Publications (1)

Publication Number Publication Date
GB1101624A true GB1101624A (en) 1968-01-31

Family

ID=23696897

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2247/66A Expired GB1101624A (en) 1965-01-25 1966-01-18 A process for the manufacture of acetylenic carbinols

Country Status (3)

Country Link
BE (1) BE675492A (en)
GB (1) GB1101624A (en)
NL (1) NL6600632A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1256560A2 (en) * 2001-05-11 2002-11-13 Basf Aktiengesellschaft Process for the preparation of higher alpha,beta-unsaturated alcohols

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

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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

Also Published As

Publication number Publication date
NL6600632A (en) 1966-07-26
BE675492A (en) 1966-07-25

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