Sodium Hypochlorite Pentahydrate as an Environmentally Benign Oxidizing Agent: Effective Synthesis of Carboxylic Acids from Primary Alcohols and Sulfones from Sulfides

The oxidation of primary alcohols, sulfides, and trifluoromethyl sulfides using sodium hypochlorite pentahydrate crystals as the oxidizing agent was investigated in detail. The optimal conditions for oxidation to the corresponding carboxylic acids, sulfones, and trifluoromethyl sulfones in high yields were determined. At a reaction medium pH of 9–10, primary alcohols in ethyl acetate and water in the presence of TEMPO or AZADOL were oxidized to aliphatic and aromatic carboxylic acids in high yields. Sulfides were oxidized to sulfones in high yields by using toluene as the solvent, and trifluoromethyl sulfides were oxidized to give the corresponding sulfones in benzotrifluoride in the presence of trifluoroacetic acid.