Vanillin → 4-(Benzyloxy)-3-methoxybenzaldehyde

Participants

Reaction Steps

Benzyl bromide (1.2 mL, 9.9 mmol) was added to a suspension of vanillin (1.0 g, 6.6 mmol) and potassium carbonate (2.7 g, 20 mmol) in acetone (10 mL) and treated according to Procedure 3. The crude product was recrystallised from EtOH to give 4-benzyloxy-3-methoxybenzaldehyde (1.0 g, 64%) as a colourless crystalline solid; mp 61-62° C.; δH (400 MHz, CDCl3) 3.95 (s, 3H, OCH3), 5.25 (s, 2H, OCH2), 6.99 (d, J5,6=8.0 Hz, 1H, H5), 7.32-7.45 (m, 7H, H2, H6, Ph), 9.84 (s, 1H, CHO); δC (100 MHz, CDCl3) 56.1, 70.8 109.3, 112.4, 126.6 127.2, 128.2, 128.7, 130.3, 136.0, 150.1, 153.6, 190.9; vmax 988, 1133, 1259, 1505, 1583, 1672 cm−1.

Provenance & Evidence