Vanillin → 4-Cyclohexylmethoxy-3-methoxybenzaldehyde

Participants

Reaction Steps

Bromomethylcyclohexane (0.78 mL, 4.2 mmol) was added to a suspension of vanillin (0.43 g, 2.8 mmol) and potassium carbonate (1.17 g, 8.47 mmol) in EtOH (7.0 mL) and treated according to Procedure 3 for 64 h. 4-Cyclohexylmethoxy-3-methoxybenzaldehyde (0.65 g, 93%) was obtained as a yellow oil; δH (400 MHz, CDCl3) 1.05 (m, 2H, CH2), 1.15-1.36 (m, 4H, CH2), 1.73 (m, 2H, CH2), 1.87-1.98 (m, 2H, CH2, CH), 3.88 (d, J=6.0 Hz, 2H, OCH2), 3.92 (s, 3H, OCH3), 6.95 (d, J5,6=8.0 Hz, 1H, H5), 7.40 (d, J2,6=2.0 Hz, 1H, H2), 7.42 (dd, J5,6=8.0, J2,6=2.0 Hz, 1H, H6), 9.84 (s, 1H, CHO); δC (100 MHz, CDCl3) 25.6, 26.4, 29.8, 37.3, 56.1, 74.5, 109.3, 111.4, 126.8, 129.8, 149.9, 154.4, 190.9; vmax 1133, 1265, 1508, 1586, 1683, 2853, 2925 cm−1.

Provenance & Evidence