Ethanol → Benzoic acid, 3,5-dihydroxy-, ethyl ester

Participants

Reaction Steps

To a solution of 3,5-dihydroxy benzoic acid, 1 (19 g, 123 mmol) in dry ethanol (250 mL) was added 2-3 mL of concentrated sulphuric acid drop wise and refluxed for 8 h. Ethanol was evaporated on rotavapor, diluted with water and extracted with ether. Combined ethereal layers were again washed with saturated sodium bicarbonate solution, water and dried over sodium sulphate, filtered and evaporated to dryness to afford 3. Yield 16.8 g (75%); mp 128-130° C.; MS (FAB) 183 (M++1); IR (KBr) 3496, 1819, 1687; 1H NMR (200 MHz, DMSO-d6) δ 9.89 (s, 2H), 7.06 (d, J=2.2 Hz, 2H), 6.69 (t, J=2.2 Hz, 1H), 4.48 (q, J=7.1 Hz, 2H), 1.52 (t, J=7.1 Hz, 3H).

Provenance & Evidence