Acetic Acid → 6-(4-Aminobenzene-1-sulfonyl)hexan-1-ol

Participants

Reaction Steps

A mixture of 145 g (0.47 mol) of (4-acetamidophenyl)-(6-acetoxyhexyl)sulfide and 600 mL of glacial acetic acid was heated at reflux with stirring, and 140 g (1.2 mol) of 30% hydrogen peroxide was added in small portions over 3 hours. The reaction mixture was poured on ice, and an oil separated. The mixture was extracted with dichloromethane and the extract was washed with water. The organic layer was dried (MgSO4) and the solvent was removed at reduced pressure to leave a tan oil. The oil was dissolved in a mixture of 100 g of sodium hydroxide, 260 mL of ethanol, and 140 mL of water, and refluxed with stirring for 16 hours. The product was extracted with ethyl ether and the extract was dried (MgSO4) and concentrated. A waxy solid was obtained which was recrystallized from 60% ethanol/40% water at -20° C. to provide 74 g (61%) of a tan solid.

Provenance & Evidence