2-Phenylbutyric Acid → 4'-(1-Oxo-2-phenylbutyl)methanesulfonanilide

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Reaction Steps

Methanesulfonanilide (40 g., 0.234 mole) is added over a 10 minute period with stirring to polyphosphoric acid (400 g.) heated to 90°-100°C. Heating and stirring are continued for additional 10 minutes, at which time 2-phenylbutanoic acid (36.0 g., 0.219 mole) is added portionwise during 20 minutes. After heating and stirring for 10 minutes, the solution is poured into water (600 ml.) and ice (400 g.) with stirring. The water is decanted and ethyl ether (200 ml.) is added to the remaining oil with stirring. After cooling in ice water, the product crystallizes and is collected: 18.4 g., m.p. 143°-147°C. Recrystallization from isopropanol yields 15.7 g. (23% yield), m.p. 148°-150°C.

Provenance & Evidence