Acetic Anhydride → N-(3-ethynylphenyl)acetamide

Participants

Reaction Steps

To a 250 ml 3-neck flask fitted with a condenser, nitrogen inlet and outlet, and magnetic stirrer was added 150 ml of acetic acid and 35 ml of acetic anhydride. The mixture was heated to reflux under nitrogen and cooled under nitrogen. To the cooled mixture was added 15 g (0.114 mole) of 3-aminophenylacetylene and the homogeneous solution was refluxed overnight. The cooled reaction mixture was transferred to a 500 ml one-neck flask, and the acetic acid was removed by a rotor-evaporator under high vacuum. Water (200 ml) was added to the residual oil to crystallize the solid product. The material was isolated by filtration and washed with water and then air dried. Recrystallization from carbon tetrachloride with 200 g/10 g solid plus charcoal yielded 14.4 g (79% yield) of a white crystalline product (m.p. 94°-96° C.).

Provenance & Evidence