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

Reaction equation

[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([O:9][CH3:10])[CH:5]=[CH:4][C:3]=1[C:11](=[O:19])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH3:20]N(CN(C)C)C.C(OC(=O)C)(=O)C>>[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([O:9][CH3:10])[CH:5]=[CH:4][C:3]=1[C:11](=[O:19])[C:12]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[CH2:20]

Participants

Reactant 3

HCID 5829N,N,N',N'-Tetramethylmethanediamine

HCID 7918Acetic Anhydride

HCID 111301952,3-Dichloro-4-phenylacetylanisole

Product 1

HCID 109248102,3-Dichloro-4-(2-phenylacryloyl)anisole

Procedure

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.