Oxidation of Alcohols with t-Butyl Chromate. I. The Oxidation of Primary Aliphatic Alcohols

Oxidation with t-butyl chromate has been carried out on the straight-chain alcohols with the general formula of R·CH2OH, where R is CH3, CH3(CH2)2, CH3(CH2)3, CH3(CH2)4, CH3(CH2)10, CH3(CH2)14 and CH3(CH2)16, on branched-chain alcohols with a variety of substituents at the carbon alpha or beta to the hydroxymethyl group, and on unsaturated alcohol with an allylic hydroxymethyl group. Thus, a saturated primary alcohol containing the grouping of –CH2·CH2OH, >CH·CH2OH or (Remark: Graphics omitted.)C·CH2OH has been found to produce mixtures of the corresponding aldehyde, acid and ester in comparable yields. On the other hand, an unsaturated primary alcohol with an olefinic double bond on the carbon adjacent to the hydroxymethyl group produces the corresponding aldehyde in a high yield, but not the ester.