(3,4-Dimethoxyphenyl)acetic acid → (3,4-Dimethoxyphenyl)acetyl chloride

Participants

Reaction Conditions

Reaction Steps

To a solution of 20 g. (0.10 mole) of 3,4-dimethoxyphenylacetic acid in 100 ml. of benzene was added dropwise 70 ml. (115 g., 0.98 mole) of thionyl chloride. The solution was heated to 50° C. for two hours, then evaporated in vacuo to give a residue of 3,4-dimethoxyphenylacetyl chloride. A solution of 21.4 g. (0.10 mole) of the acid chloride in 70 ml. of chloroform was added with stirring to a solution of 70 ml. of chloroform and 22.2 ml. (30.0 g., 0.30 mole) of N,N-di-(n-propyl)amine at 0° C. The resulting mixture was heated at 50° C. for two hours, cooled, diluted and washed with dilute hydrochloric acid, dilute sodium carbonate solution and water. The dried chloroform solution was evaporated in vacuo to give N,N-di(n-propyl)-3,4-dimethoxyphenylacetamide.

Provenance & Evidence