Veratraldehyde → 39964-87-9

Participants

Reaction Steps

3,4-Dimethoxybenzaldehyde (12.20 g, 73.42 mmol) was dissolved in benzene (200 mL) and aminoacetaldehyde dimethyl acetal (12.0 mL, 11.7 g, 111 mmol) was added. The mixture was stirred at reflux for 4 h using a Dean-Stark trap. The reaction mixture was then concentrated and dissolved in CHCl3 (250 mL). The solution was washed with water (4×150 mL) and brine (150 mL), dried (Na2SO4) and concentrated, and the last traces of solvent were removed under vacuum to provide the imine (18.41 g, 99.1%) as a light yellow solid: mp 50-52° C. 1H NMR (300 MHz, CDCl3) δ 8.18 (s, 1H), 7.42 (s, 1H), 7.15 (d, J=8.4 Hz, 1H), 6.86 (d, J=8.4 Hz, 1H), 4.65 (t, J=5.1 Hz, 1H), 3.92 (s, 3H), 3.90 (s, 3H), 3.74 (d, J=5.1 Hz, 2H), 3.40 (s, 6H).

Provenance & Evidence