Dimethyl Sulfate → Methyl 3-(4-formylphenyl)-2-propenoate

Participants

Reaction Steps

A suspension of 4-formylcinnamic acid (10.0 g), dimethyl sulfate (5.9 ml) and potassium carbonate (11.8 g) in 100 ml dimethylformamide was stirred at room temperature for 17 hours. After removal of inorganic salts by filtration, saturated aqueous sodium bicarbonate was added to the reaction mixture, which was then extracted twice with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate and brine, and dried over sodium sulfate. The drying agent was filtered off and the filtrate was evaporated and dried under reduced pressure to give methyl 4-formylcinnamate (9.78 g, 91%) as a pale yellow solid.

Provenance & Evidence