Hydrochloric Acid → 2-(Benzyloxy)-5-formylbenzoic acid

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Reaction Steps

Lithium hydroxide (3.38 g, 0.14 mol, 3 eq) in water (50 mL) was added to a stirred solution of benzyl 2-benzyloxy-5-formylbenzoate (16.13 g, 0.046 mol, 1 eq) in a mixture of tetrahydrofuran (200 mL) and methanol (50 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 (200 mL), and the organic solution washed with brine (200 mL), then extracted with saturated aqueous sodium bicarbonate (3×200 mL). The basic solution was washed with ethyl acetate (200 mL), then acidified to pH 1 with 10% HCl and back extracted with ethyl acetate (3×200 mL). The organic solution was dried over sodium sulfate and evaporated in vacuo to give a pale yellow powder (10.83 g, 89%). 1H NMR (CDCl3) δ9.94 (s, 1H, O═C—H), 5.37 (s, 2H, CH2Ph).

Provenance & Evidence