Dimethylformamide → 2-(4-Chlorophenyl)-3-(dimethylamino)acrylaldehyde

Participants

Reaction Steps

Dimethylformamide (81 grams) was added dropwise to phosphorus oxychloride (138 grams) keeping the temperature at 20°-30° C. by external cooling. The mixture was stirred for 15 minutes at room temperature and then 4-chlorophenylacetic acid (50 grams in 30 ml DMF) was added. After heating to 65°-75° C. for 20 hours, the reaction mixture was cooled, poured onto 1 kilogram of ice and made basic to pH 12 with 50% sodium hydroxide, and then heated on a steam bath for 1 hour. The precipitate which formed was filtered, washed with water, dried in vacuo, and then recrystallized from ethyl acetate yielding the desired product, m.p. 117°-120° C.

Provenance & Evidence