Continuous Flow Oxidation of Alcohols and Aldehydes Utilizing Bleach and Catalytic Tetrabutylammonium Bromide

Organic Process Research & Development 16(5),1082-1089, DOI: 10.1021/op200118h

We report a method for the oxidation of a range of alcohols and aldehydes utilizing a simple flow system of alcohols in EtOAc with a stream of 12.5% NaOCl and catalytic Bu4NBr. Secondary alcohols are oxidized to ketones, aldehydes are oxidized directly to methyl esters in the presence of methanol, and benzylic alcohols are oxidized to either benzaldehydes or methyl esters, depending on the conditions used. The reaction conditions are mild and generally provide complete conversion in 5–30 min.