GB947419A - Unsaturated bis-tertiary glycols and processes for their production - Google Patents

Unsaturated bis-tertiary glycols and processes for their production

Info

Publication number
GB947419A
GB947419A GB28996/61A GB2899661A GB947419A GB 947419 A GB947419 A GB 947419A GB 28996/61 A GB28996/61 A GB 28996/61A GB 2899661 A GB2899661 A GB 2899661A GB 947419 A GB947419 A GB 947419A
Authority
GB
United Kingdom
Prior art keywords
formula
phenyl
halogen atom
acetylene
reacted
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
GB28996/61A
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.)
Novartis AG
Original Assignee
JR Geigy 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 JR Geigy AG filed Critical JR Geigy AG
Publication of GB947419A publication Critical patent/GB947419A/en
Expired legal-status Critical Current

Links

Classifications

    • 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

Landscapes

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

Abstract

The invention comprises unsaturated bistertiary glycols of the general formula: <FORM:0947419/C2/1> wherein R represents a hydrogen atom or the methyl group, X represents a halogen atom or the trifluoromethyl group, Y represents a hydrogen atom or a halogen atom and each Z represents hydrogen or, together, they represent an additional bond; and their preparation by (I) reacting a 2-phenyl acetoin of formula: <FORM:0947419/C2/2> with at least 1 molar excess of an organometallic compound of formula: <FORM:0947419/C2/3> wherein M is the group Hal-Mg-, where Hal is a halogen atom, or when the two symbols z together represent an additional bond M may also be lithium, sodium or potassium, and then hydrolysing the reaction product obtained, and (z) optionally hydrogenating in the presence of a hydrogenation catalyst an acetylene of formula I to an ethylene. Metal acetylides III may be formed directly in liquid ammonia or during reaction from the alkyne and a suspended alkali metal hydroxide. Organic magnesium halides III may be prepared in tetrahydrofuran, for example reacting ethyl magnesium bromide with acetylene. 2-Phenyl-acetoins II may be prepared from phenyl magnesium bromides reacted with diacetyl or from acetophenones reacted with acetylides to give a product to which water is added.
GB28996/61A 1960-08-30 1961-08-11 Unsaturated bis-tertiary glycols and processes for their production Expired GB947419A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH976860A CH390235A (en) 1960-08-30 1960-08-30 Process for the production of unsaturated bis-tertiary glycols

Publications (1)

Publication Number Publication Date
GB947419A true GB947419A (en) 1964-01-22

Family

ID=4355468

Family Applications (1)

Application Number Title Priority Date Filing Date
GB28996/61A Expired GB947419A (en) 1960-08-30 1961-08-11 Unsaturated bis-tertiary glycols and processes for their production

Country Status (5)

Country Link
BE (1) BE607678A (en)
CH (1) CH390235A (en)
DE (1) DE1180734B (en)
ES (1) ES270161A1 (en)
GB (1) GB947419A (en)

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1073477B (en) * 1960-01-21 Lovens kemiske Fabrik ved A. Kongsted, Kopenhagen Process for the production of 2-phenyl- and 2-p-chlorophenyl- 3-methyl-2,3-dihydroxy-hexene- (5) effective as sedatives
DE1082251B (en) * 1958-01-02 1960-05-25 Leo Pharm Prod Ltd Process for the production of phenyl alkynediols

Also Published As

Publication number Publication date
DE1180734B (en) 1964-11-05
BE607678A (en) 1962-02-28
ES270161A1 (en) 1962-03-01
CH390235A (en) 1965-04-15

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