Methanol → Methyl 3-hydroxy-4-methoxybenzoate

Participants

Reaction Steps

To a suspension of 3-hydroxy-4-methoxy benzoic acid (33.63 g, 0.2 mol) in MeOH (500 ml) was added concentrated sulphuric acid (25 ml) and the reaction mixture was heated to reflux for 2 h. On cooling the reaction mixture was concentrated under reduced pressure to 100 ml and the residue was extracted with EtOAc. The organic layer was washed sequentially with H2O (×2), saturated aqueous sodium bicarbonate and saturated brine, dried over MgSO4 and evaporated under reduced pressure, to afford the subtitle compound as colourless crystals (33.0 g, 91%). Rf 0.59 (EtOAc). MS m/z 183 (MH+).

Provenance & Evidence