Methanol → 3-Benzyloxybenzaldehyde

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To a solution of 3-hydroxylbenzaldehyde 31 (5.0 g, 40 mmol) and K2CO3 (27.2 g, 197 mmol) in 200 ml CHCl3: 100 ml MeOH was added benzylbromide (5.9 ml, 49 mmol). The suspension was refluxed under nitrogen overnight. The solvent was removed by evaporation and the resulting oil was taken up in DCM and washed with water and brine and dried (Na2SO4). The crude product was purified by column chromatography to yield the product as a viscous oil which solidified upon sitting (8.48 g, 40 mmol, 98%). m.p. 46°. 1H NMR (500 MHz, CDCl3) δ 9.97 (s, 1H), 7.48-7.25 (m, 9H), 5.13 (s, 2H). 13C NMR (125 MHz, CD3OD) δ 191.8, 159.2, 137.8, 136.3, 130.0, 128.6, 128.1, 127.5, 123.41, 121.9, 113.3, 70.0. HRMS (EI) m/e calcd for C14H12O2: 212.08373, found: 212.0827.

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