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Selective oxidation of primary-secondary diols with methyl hypochlorite in acid buffered medium

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
51
Issue
43
Identifiers
DOI: 10.1016/0040-4020(95)00747-v

Abstract

Abstract A convenient, low cost method was developed for the selective oxidation of secondary alcohols, leaving primary alcohol functions intact. Methyl hypochlorite, generated from chlorine or trichloroisocyanuric acid in methanol, is used as a ‘positive chlorine’ reagent in the presence of an appropriate buffer which is acidic enough to warrant good transfer of ‘positive chlorine’. 1,9( R)-octadecanediol was converted to 1 -hydroxy-9-octadecanone with 98% selectivity.

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