3-(4-Hydroxy-3-Methoxyphenyl)Prop-2-Enoic Acid → Methyl Ferulate

Participants

Reaction Conditions

Reaction Steps

100 g of 4-hydroxy-3-methoxycinnamic acid were dissolved in 1 l of methanol and treated with 14.4 ml of concentrated sulphuric acid. The solution was heated under reflux for 2.5 hrs. Subsequently, the majority of the methanol (about 750 ml) was distilled off and the residue remaining was poured into 1 l of water. Then, the mixture was extracted three times with 500 ml of ethyl acetate each time and the organic phases were combined, washed twice with 250 ml of 10% sodium bicarbonate solution each time, dried over sodium sulphate, filtered and evaporated. The residue was dissolved in 800 ml of methanol, filtered and, for crystallization, cooled to -25° C. The crystals were thereupon filtered off under suction, washed with 100 ml of cold methanol and dried in a high vacuum at room temperature. This gave 54.7 g of yellowish colored crystals.

Provenance & Evidence