Methyl 4-Formylbenzoate → HCID 329156, compound

Participants

Reaction Steps

To a stirred solution of diethyl cyanomethylphosphonate (96 ml) in 1,2-dimethoxyethane (375 ml) was added sodium hydride (60% : 22g) portionwise below 5° C. and the stirring was continued at 0° C. for half an hour and then at ambient temperature for half an hour. The reaction mixture was recooled to 0° C. and a solution of methyl p-formylbenzoate (75 g) in 1,2-dimethoxyethane (375 ml) was added to the reaction mixture below 6° C. The reaction mixture was quenched with saturated aqueous sodium bicarbonate and diluted with ethyl acetate. The organic layer was washed with water and aqueous saturated sodium bicarbonate and dried over magnesium sulfate and filtered. The solvent was removed in vacuo and the solid product was recrystallized from ethanol to give 4-methoxycarbonylcinnamonitrile (52.12 g) as a white needle.

Provenance & Evidence