Hydrochloric Acid → 5-Formyl-2-methoxybenzoic acid

Participants

Reaction Steps

Lithium hydroxide (1.04 g, 0.043 mol, 3 eq) in water (10 mL) was added to a stirred solution of methyl 2-methoxy-5-formylbenzoate (2.8 g, 0.014 mol, 1 eq) in a mixture of tetrahydrofuran (30 mL) and methanol (20 mL). The solution was stirred overnight, acidified to pH 1 with 10% HCl and the organic solvents removed in vacuo. The aqueous solution was extracted with ethyl acetate (100 mL) and the organic solution washed with brine (100 mL), then extracted with saturated aqueous sodium bicarbonate (3×100 mL). The basic solution was washed with ethyl acetate (100 mL), then acidified to pH 1 with 10% HCl and back extracted with dichloromethane (3×100 mL). The organic solution was dried over sodium sulfate and evaporated in vacuo to give a cream coloured powder (2.01 g, 77%). 1H NMR (CDCl3) δ9.99 (s, 1H, O═C—H), 4.14 (s, 3H, CH3).

Provenance & Evidence