Dimethylformamide → 3-(p-Diethylaminophenyl)-3-phenylacrolein

Participants

Reaction Steps

After adding dropwise 3.9 g of phosphorus oxychloride to a solution of 2.2 g of dimethylformamide (DMF) and 50 ml of 1,2-dichloroethane at from 0° to 5° C., the mixture was stirred at that temperature for 30 minutes. Then, a solution of 5.2 g of 1-(p-diethylaminophenyl)-1-phenylethylene in 50 ml of 1,2-dichloroethane solution was added dropwise thereto at that temperature over 30 minutes, and the mixture was reacted from 5 hours at room temperature. Hydrolysis was conducted with an addition of 100 cc of water containing 10 g of sodium acetate. After separating and water-washing an organic layer, the solvent was distilled off to obtain 4.8 g of an oily substance which was subsequently separated and purified on silica gel column chromatography to obtain 3.3 g (yield: 57% (theory)) of an oily product.

Provenance & Evidence