GB751056A - Substituted propynyl-carbinols and process for the manufacture thereof - Google Patents

Substituted propynyl-carbinols and process for the manufacture thereof

Info

Publication number
GB751056A
GB751056A GB16444/54A GB1644454A GB751056A GB 751056 A GB751056 A GB 751056A GB 16444/54 A GB16444/54 A GB 16444/54A GB 1644454 A GB1644454 A GB 1644454A GB 751056 A GB751056 A GB 751056A
Authority
GB
United Kingdom
Prior art keywords
propyn
carbinol
propynyl
chlormethyl
bromide
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
GB16444/54A
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.)
Roche Products Ltd
Original Assignee
Roche Products 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 Roche Products Ltd filed Critical Roche Products Ltd
Publication of GB751056A publication Critical patent/GB751056A/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 propynyl carbinols of the general formula <FORM:0751056/IV(a)/1> wherein R is a methyl, ethyl or chlormethyl group and R1 is a chlormethyl or 2-chlorethyl group, and their manufacture by reacting a propynyl halide, preferably the bromide, with a ketone R-CO-R1 in the presence of zinc and hydrolysing the zinc compound so obtained. The reaction is preferably carried out in an inert solvent such as dry ether or ether/benzene at a temperature of about 40 DEG C., and the hydrolysis may be accomplished with dilute mineral acid, water, ammonium salt solutions or an organic acid. The primary reaction may be initiated by the addition of a trace of iodine. In examples: (1) propynyl bromide and dichloracetone give dichlormethyl-propyn-(2)-yl-carbinol; (2) propynyl bromide and chloracetone give methylchlormethyl - propyn - (2) - yl - carbinol; (3) propynyl bromide and 1-chlorobutanone-(2) give ethyl - chlormethyl - propyn - (2) - yl - carbinol; (4) Propynyl bromide and 1 - chlorbutanone - (3) give methyl - (2 - chlorethyl) - propyn - (2) - yl - carbinol. Similarly chlormethyl - (2 - chlorethyl) - propyn - (2) - yl - carbinol is obtained from 1,4 - di - chlor - butanone - (2) and ethyl-(2 - chloroethyl) - propyn - (2) - yl carbinol is obtained from 1-chlorpentanone-(3).
GB16444/54A 1953-06-12 1954-06-03 Substituted propynyl-carbinols and process for the manufacture thereof Expired GB751056A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH751056X 1953-06-12

Publications (1)

Publication Number Publication Date
GB751056A true GB751056A (en) 1956-06-27

Family

ID=4533879

Family Applications (1)

Application Number Title Priority Date Filing Date
GB16444/54A Expired GB751056A (en) 1953-06-12 1954-06-03 Substituted propynyl-carbinols and process for the manufacture thereof

Country Status (1)

Country Link
GB (1) GB751056A (en)

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