Dimethylformamide → 4,4'-Bis(carbomethoxy)stilbene

Participants

Reaction Steps

DMF (100 mL) and methyl 4-formylbenzoate (13.9 g, 0.13 mole) are added to the product solution from step (3) at a temperature of 25° to 28° C. Sodium methoxide (7 g) is added to the solution while maintaining the temperature at 25° to 35° C. by means of a water bath. The reaction mixture is heated at 25° to 35° C. for an additional 4 hours and then water (100 mL) is slowly added at 25° to 35° C. (with water bath cooling as necessary) to precipitate the product. After stirring for 1 hour, the product, dimethyl 4,4'-stilbenedicarboxylate, is collected by filtration, washed with water until the filtrate has a pH of 5 to 7 and then washed with methanol (2×50 mL). After drying at 60° C. under vacuum, dimethyl 4,4'-stilbenedicarboxylate is obtained in a 65% yield based on the amount of methyl 4-(hydroxymethyl)benzoate employed.

Provenance & Evidence