Phenethyl bromide → 3-Hydroxy-4-(2-phenylethoxy)benzaldehyde

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Reaction Steps

(2-Bromoethyl)benzene (20 mL, 0.14 mol, 2 eq) was added to a stirred solution of 3,4-dihydroxybenzaldehyde (10 g, 0.072 mol, 1 eq), tetra-n-butylammonium iodide (27 g, 0.072 mol, 1 eq) and cesium carbonate (14.2 g, 0.043 mol, 0.6 eq) in N,N-dimethylformamide (50 mL). The solution was stirred overnight, then concentrated in vacuo and diluted with ethyl acetate (200 mL). The organic solution was washed with 1M HCl (2×200 mL), and brine (200 mL), dried over sodium sulfate and evaporated. The residue was purified by chromatography on silica gel, eluting with toluene:ethyl acetate (19:1). This gave the product as a colourless oil which crystallized on standing (2.71 g, 15%). RF (toluene:ethyl acetate, 9:1) 0.31. 1H NMR (CDCl3) δ 9.84 (s, 1H, O═C—H), 6.96 (d, 1H, J 8.3 Hz, ArH), 5.64 (s, 1H, OH), 4.36 (t, 2H, J 7.2 Hz, OCH2CH2Ph), 3.17 (t, 2H, J 7.2 Hz, OCH2CH2Ph).

Provenance & Evidence