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

Participants

Reaction Conditions

Reaction Steps

Phosphorus oxychloride (28 ml) was added dropwise with stirring to dry dimethylformamide (38 ml) with cooling in an ice-bath to keep the temperature below 20° C. p-Chlorophenylacetic acid (17.05 g) was added, and the solution was heated to 70° C. for 6 hours and then left to stand overnight. The red solution was poured onto ice and neutralised with 40% sodium hydroxide whilst cooling in an ice/salt bath. Potassium carbonate (150 g) was added and the mixture was heated to boiling for 0.5 hour. The precipitate which formed was filtered off, washed well with water and recrystallised from carbon tetrachloride to give, as white crystals, 2-(p-chlorophenyl)-3-dimethylaminoprop-2-enal, m.p. 120° C.

Provenance & Evidence