Acetic Anhydride → (Z)-ethyl 2-acetyloxy-3-phenyl-2-propenoate

Participants

Reaction Steps

A solution containing 22 g. of ethyl phenylpyruvate, 65 g. of acetic anhydride and 20 mg. of p-toluenesulfonic acid monohydrate was refluxed for 2.5 hours. Excess acetic anhydride was stripped from the reaction mass and the product, crude (Z)-ethyl 2-acetyloxy-3-phenyl-2-propenoate, was distilled at about 1.6 mm. Hg. (b.p. 120°-135° C.). The recovered product crystallized on standing in refrigeration and was recovered by filtration and recrystallized from ethanol; recovered 12.1 g., m.p. 41°-47° C.; second recrystallization, 10.5 g., m.p. 47°-49° C.; third recrystallization, 9.2 g., m.p., 47°-49° C.

Provenance & Evidence