Methanol → Methyl Ferulate

Participants

Reaction Steps

25 g (0.13 mol) of (E)-4-hydroxy-3-methoxycinnamic acid were dissolved in 180 ml of methanol, and 5 ml of concentrated sulphuric acid were added. The solution was heated under reflux for 2 hours. The main amount of the methanol (about 150 ml) was then distilled off and the residue that remained was poured into 500 ml of ice-water. The precipitated ester was filtered off with suction, washed in succession with cold water, with a small amount of a cold saturated sodium bicarbonate solution and again with cold water and dried at 50° C. under a waterjet vacuum. Chromatography on 250 g of silica gel using dichloromethane/diethyl ether (19:1) yielded 21.78 g of (E)-4-hydroxy-3-methoxycinnamic acid methyl ester in the form of a light-yellow oil.

Provenance & Evidence