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 agents was investigated in detail. The optimal conditions for the oxidation of the corresponding carboxylic acids, sulfones, trifluoromethylsulfones in high yields were determined. By adjusting the pH of the reaction medium to 9–10, the primary alcohol in ethyl acetate and water in the presence of TEMPO or AZADOL was oxidized to aliphatic and aromatic carboxylic acids in high yields. The sulfide was oxidized to sulfone in high yield using toluene as the solvent, and trifluoromethyl sulfide was oxidized to give the corresponding sulfone in benzotrifluoride in the presence of trifluoroacetic acid.