Vanillin → HCID 59333872, 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. 3-Methoxy-4-(pent-2-ynyloxy)benzaldehyde (0.60 g, 84%) was obtained as a yellow crystalline solid; mp 47-50° C.; δH (400 MHz, CDCl3) 1.11 (t, J=7.6 Hz, 2H, CH2CH3), 2.20 (tq, J=7.6, 2.4 Hz, 3H, CH2CH3), 3.93 (s, 3H, OCH3), 4.83 (t, J=2.4 Hz, 2H, OCH2), 7.13 (d, J5,6=8.0 Hz, 1H, H5), 7.42 (s, 1H, H2), 7.45 (d, J5,6=8.0 Hz, H6), 9.86 (s, 1H, CHO); δC (100 MHz, CDCl3) 12.5, 13.4, 56.0, 57.3, 73.1, 90.7, 109.2, 112.3, 126.4, 130.5, 149.9, 152.5, 190.9; vmax 997, 1136, 1263, 1508, 1586, 1682, 2230, 2298, 2845, 2932 cm−1.

Provenance & Evidence