Vanillin → 4-Methoxy-3-[(prop-2-yn-1-yl)oxy]benzaldehyde

Participants

Reaction Steps

Propargyl bromide (2.90 mL, 80% w/v, 19.7 mmol) was added to a suspension of vanillin (2.00 g, 13.1 mmol) and potassium carbonate (5.46 g, 39.4 mmol) in acetone (20 mL) and treated according to Procedure 3. 4-Methoxy-3-propargyloxybenzaldehyde (2.01 g, 80%) was obtained as a colourless crystalline solid; mp 66-67° C.; δH (400 MHz, CDCl3) 2.54 (t, J=2.4 Hz, 1H, C≡CH), 3.95 (s, 3H, OCH3), 4.81 (d, J=2.4 Hz, 1H, OCH2), 7.00 (d, J5,6=8.4 Hz, 1H, H5), 7.50-7.53 (m, 2H, H2, H6), 9.85 (s, 1H, CHO); δC (100 MHz, CDCl3) 56.1, 56.6, 76.4, 77.6, 110.9, 111.9, 127.3, 129.9, 147.3, 154.9, 190.6; HRMS (ESI) Calculated for C11H10O3 [M+H]+ 191.0703. found 191.0704; vmax 1014, 1130, 1261, 1584, 1678, 2119, 2841, 2932, 3262 cm−1.

Provenance & Evidence