N,N,N',N'-Tetramethylmethanediamine → 2,3-Dichloro-4-(2-phenylacryloyl)anisole

Participants

Reaction Steps

2',3' -Dichloro-4'-methoxy-2-phenylacetophenone (300 g.) is suspended in 1000 ml. of N,N,N,N-tetramethylmethanediamine at 25°C. under nitrogen, and acetic anhydride (1000 ml.) is added dropwise. The reaction mixture is maintained below 40°C. by cooling in an ice-water bath and regulating the rate of anhydride addition. The reaction mixture is left at 25°C. for 1 hour then slowly added to crushed ice-water (8 liters) with stirring. The white solid precipitate is collected by suction filtration, washed with water, and air-dried at 25°C. for 2 days. Yield: 310.5 g. (99%), mp 87°-89°C. A sample recrystallized from benzene-hexane melts at 87°-89°C.

Provenance & Evidence