Acetic Anhydride → N-(3-ethynylphenyl)acetamide

Participants

Reaction Steps

A 30.0 g (0.256 mole) sample of 3-aminophenylacetylene was cooled at ice bath temperature and 27.0 ml (0.282 mole) of acetic anhydride was added dropwise. The ice bath was removed and the mixture stirred for 30 min. The mixture was diluted with ether and the resulting solution washed with water, NaHCO3 solution and brine. The organic phase was dried (K2CO3) and the solvent evaporated in vacuo. The crystalline residue was recrystallized from CHCl3 -hexane to give 60.7 g (89% yield) of crystalline N-(3-ethynylphenyl)acetamide, mp 94°-96° C.

Provenance & Evidence