Practical and Chemoselective Reduction of Acyl Chloride to Alcohol by Borohydride in Aqueous Dichloromethane

A simple methodology for the reduction of acid chlorides to their corresponding alcohols has been developed. Various carboxylic acids were converted to alcohols in excellent yields using NaBH 4 -K 2 CO 3 in a mixed solvent system of dichloromethane and water (1:1) in the presence of a phase-transfer...

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Bibliographic Details
Published inSynthetic communications Vol. 40; no. 19; pp. 2897 - 2907
Main Authors Rajan, Ramya, Badgujar, Sachin, Kaur, Kamaljit, Malpani, Yashwardhan, Kanjilal, Pranab R.
Format Journal Article
LanguageEnglish
Published PHILADELPHIA Taylor & Francis Group 31.08.2010
Taylor & Francis
Taylor & Francis Ltd
Subjects
Acyl chloride
Alcohol
aqueous dichloromethane
base
borohydride
Chemistry
Chemistry, Organic
phase-transfer catalyst
Physical Sciences
Science & Technology
alcohol
SYSTEM
HALIDES
PHASE-TRANSFER CATALYSIS
POLYETHYLENE GLYCOLS
phase-transfer catalyst
SODIUM-BOROHYDRIDE
KETONES
REDUCING AGENT
ESTERS
Acyl chloride
borohydride
FUNCTIONAL-GROUPS
aqueous dichloromethane
base
CARBOXYLIC-ACIDS
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Summary:A simple methodology for the reduction of acid chlorides to their corresponding alcohols has been developed. Various carboxylic acids were converted to alcohols in excellent yields using NaBH 4 -K 2 CO 3 in a mixed solvent system of dichloromethane and water (1:1) in the presence of a phase-transfer catalyst at low temperature. The importance of the work is its simplicity, selectivity, excellent yield, and very short reaction time. This new reduction condition has proved to be an excellent chemoselective method for a range of acid chlorides in the presence of various functional groups.
ISSN:0039-7911
1532-2432
DOI:10.1080/00397910903340645