Hydrochloric Acid → 1-[4-(Methylsulfanyl)phenyl]propan-2-one

A stirred mixture of crude 1-methylsulfanyl-4-(2-nitro-propenyl)-benzene (27a) (28.8 mmol) iron filings (6.25 g, 112 mmol) and ferric chloride hexahydrate (0.155 g, 0.57 mmol) in water (20 ml) is heated to reflux. Concentrated hydrochloric acid (10 ml) is added over 2 hours the reflux continued for 4 hours. After 18 hours at room temperature the reaction is diluted with water and chloroform. The mixture is filtered through celite and the organic extract is separated. The aqueous extract is extracted with chloroform and the combined organic extracts are dried (MgSO4). The solvent is removed and the residue is purified by chromatography on silica eluting with hexane-ethyl acetate (3:1) to afford the title compound (2.65 g).