Dimethylformamide → 2-(3,4-Dichlorophenoxy)-3-(dimethylamino)prop-2-enal

反応式

O=P(Cl)(Cl)Cl.C([O:8][CH:9](OCC)[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=1)C.C(=O)([O-])[O-].[K+].[K+].[CH3:29][N:30]([CH3:33])[CH:31]=O>>[Cl:19][C:14]1[CH:13]=[C:12]([CH:17]=[CH:16][C:15]=1[Cl:18])[O:11][C:10](=[CH:29][N:30]([CH3:33])[CH3:31])[CH:9]=[O:8]

参加物

反応物 4

HCID 6228Dimethylformamide

HCID 11430Potassium Carbonate

HCID 24813Phosphorus oxychloride

HCID 27820221,2-Dichloro-4-(2,2-diethoxyethoxy)benzene

生成物 1

HCID 545558182-(3,4-Dichlorophenoxy)-3-(dimethylamino)prop-2-enal

実験手順

Dimethylformamide (29.2 g) was slowly added to 122.7 g of POCl3 in a reaction flask. After the addition was complete, the mixture was heated to 80° C. while 3,4-dichlorophenoxyacetaldehyde diethyl acetal (55.8 g) was added, and the resulting mixture was then heated for an additional two hours at about 80°-85° C. The reaction mixture was cooled to room temperature and poured into about 400 g of potassium carbonate in an ice-water mixture and then extracted with methylene chloride. The methylene chloride extract was then dried and concentrated to a dark oil which solidified upon dilution with ethyl acetate. 22.1 g of the desired, 2-(3,4-dichlorophenoxy)-3-dimethylamino-propenal was obtained and subsequently identified by NMR spectroscopy.