Methanol → Methyl Ferulate

Participants

Reaction Steps

25 g (0.13 mmol) of (E)-4-hydroxy-3-methoxycinnamic acid was dissolved in 180 ml of methanol, and 5 ml of concentrated sulfuric acid was added thereto. The solution was heated at reflux for 2 hours. The majority of the methanol (about 150 ml) was removed by distillation and the remaining residue was poured into 500 ml of ice-water thereby to effect precipitation of the ester, which was then purified by suction filtration and washed firstly with cold water, then with a small amount of cold saturated sodium bicarbonate solution and finally with cold water and dried at 50° C. under a water-jet vacuum. The product was then purified by chromatography using silica gel (250 g) using dichloromethane:diethyl ether (19:1) as eluant to give 21.78 g of (E)-4-hydroxy-3-methoxycinnamic acid methyl ester in the form of a light-yellow oil.

Provenance & Evidence