Vanillin → HCID 59333855, compound

Participants

Reaction Steps

1-Bromopent-2-yne (0.67 mL, 6.6 mmol) was added to a suspension of vanillin (0.50 g, 3.3 mmol) and potassium carbonate (1.37 g, 9.85 mmol) in acetone (5.0 mL) and treated according to Procedure 3. 4-Methoxy-3-(pent-2-ynyloxy)benzaldehyde (0.69 g, 96%) was obtained as a yellow crystalline solid; mp 38-39° C.; δH (400 MHz, CDCl3) 1.10 (t, J=7.6 Hz, 2H, CH2CH3), 2.20 (tq, J=7.6, 2.0 Hz, 3H, CH2CH3), 3.95 (s, 3H, OCH3), 4.79 (t, J=2.0 Hz, 2H, OCH2), 6.99 (d, J5,6=8.0 Hz, 1H, H5), 7.49 (dd, J5,6=8.0, J2,6=2.0 Hz, 1H, H6), 7.54 (d, J2,6=2.0 Hz, 1H, H2), 9.85 (s, 1H, CHO); δC (100 MHz, CDCl3) 12.5, 13.5, 56.1, 57.3, 73.4, 90.5, 110.7, 111.8, 126.9, 129.9, 147.6, 154.8, 190.8; vmax 1007, 1130, 1261, 1508, 1583, 1683, 2230, 2290, 2841, 2976 cm−1.

Provenance & Evidence