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

Participants

Reaction Steps

To a solution of 2,4-dihydroxybenzaldehyde (100 g, 0.72 mol) in CH3CN (1.5 L), NaHCO3 (72.0 g, 0.86 mol) and benzyl bromide (145.4 g, 0.85 mol) were added and the reaction mixture was stirred under reflux. The reaction progression was followed by TLC and on completion the reaction mixture was cooled to room temperature and filtered. The organic solvents were evaporated under vacuum. The off white residue was recrystallized from MeOH to obtain 4-benzyloxy-2-hydroxybenzaldehyde (B2a) (140 g, 0.61 mol) in 85% yield: mp 77-79° C. [lit.42 mp 78-80° C.); TLC Rf 0.73 [EtOAc/hexanes (1:2)]; ((CD3)2CO, 600 MHz) δ 11.50 (1H, s), 9.88 (1H, br), 7.67 (1H, d, J=5.4 Hz), 7.50 (2H, d, J=7.2), 7.41 (2H, m), 7.36 (1H, m), 6.71 (1H, m), 6.57 (1H, s), 5.24 (2H, s).

Provenance & Evidence