2,4-Dihydroxybenzaldehyde → 4-Benzyloxy-2-hydroxybenzaldehyde

Participants

Reaction Steps

To a solution of the 2,4-dihydroxybenzaldehyde (100 g, 0.67 mol) in CH3CN (1 L), BnBr (112.4 g, 0.67 mol) and NaHCO3 (90.8 g, 0.67 mol) were added. The reaction mixture was refluxed for 48 h and was monitored by TLC. Upon completion, the white precipitate was filtered and the filtrate was evaporated under vacuum. The residue was dissolved in MeOH (500 mL) and was precipitated at 0° C. The precipitates were further recrystallized from MeOH to obtain 4-Benzyloxy-2-hydroxybenzaldehyde (G3a) (127.5 g, 0.56 mol, 84%) as an off-white solid: mp 80-82C (Lit.10 78-80° C.); 1H NMR (DMSO, 400 MHz) δ 10.99 (1H, s), 9.99 (1H, s), 7.37 (5H, m), 6.61 (1H, m), 6.54 (1H, d), 5.15 (2H, s).

Provenance & Evidence