Methanol → Methyl 3,5-Dihydroxybenzoate

Participants

Reaction Steps

A solution of 3,5-dihydroxybenzoic acid (20.0 g, 129.9 mmol) in dry methanol (100 mL) and H2SO4 (1 mL) was refluxed for 20 h. The volatile product was removed in vacuo and the residue was redissolved in ethyl acetate (EA) and washed with aqueous NaHCO3, water and brine. The organic phase was dried with anhydrous sodium sulphate and the solvent was evaporated to yield methyl 3,5-dihydroxybenzoate as a white colored solid (95% yield, m.p.=170° C.). 1H-NMR (300 MHz, CDCl3) δ 7.1 (d, 2H), 6.6 (t, 1H), 4.9 (s, OH), 3.9 (s, OCH3).

Provenance & Evidence