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

Participants

Reaction Steps

Anhydrous sodium bicarbonate (1 g, 12 mmol) was added to a solution of 2,4-dihydroxybenzaldehyde (1.38 g, 10 mmol) in 50 mL of acetonitrile and the mixture was stirred for 1 hour at RT. Benzylbromide (1.2 mL, 10 mmol) was added and the mixture was refluxed for 6 hours. After disappearance of the reactant (TLC), the reaction was poured into ice water with vigorous stirring. A white solid precipitated and it was recrystallized from methanol (ca. 40 mL) to obtain (1.82 g, 80 of P1 as a white powder: mp 78-80° C.; TLC Rf 0.88 in toluene:methanol (10:1); 1H NMR (600 MHz, acetone-d6) δ 11.41 (s, 1H, OH), 9.81 (s, 1H, CHO), 7.67 (d, 1H, J=8.4 Hz, Ar—H6), 7.45-7.35 (m, 5H, C6H5), 6.70 (dd, 1H, 2J=8.4 Hz, 3J=2.4 Hz, Ar—H5), 6.56 (d, 1H, J=1.8 Hz, Ar—H3), 5.24 (s, 2H, PhCH2).

Provenance & Evidence