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

Article abstract of DOI:10.1016/0040-4020(95)00747-V

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.