Methanol → 4-(2-Methoxyethyl)phenol

Participants

Reaction Conditions

Reaction Steps

A mixture of 80 grams of 4-hydroxyphenethyl alcohol (0.58 moles), methanol (100 ml), and 10 grams of Dowex 50 catalyst (H30 form, washed with methanol) was charged into a 300 cc autoclave. The autoclave was sealed, purged with nitrogen and then pressurized under nitrogen. The autoclave was heated to 150° C. overnight with stirring (about 16 hours). The reactor was then cooled, depressurized, and purged with nitrogen to remove by-product dimethyl ether. The catalyst was filtered off and a few drops of saturated aqueous sodium bicarbonate solution were added to neutralize acidity. The solvent was removed on a rotary evaporator. The product was isolated in 65% yield by distillation, with 33% of the 4-hydroxyphenethyl alcohol remaining unreacted.

Provenance & Evidence