4-Hydroxybenzaldehyde → p-Dodecyloxybenzaldehyde

Participants

Reaction Steps

4-Hydroxybenzaldehyde (5.0 g, 41 mmol, 1.0 equiv.), potassium carbonate (8.5 g, 61 mmol, 1.5 equiv.), dodecyl bromide (12.3 g, 49.2 mmol, 1.20 equiv.), and 18-crown-6 (1.0 g, 4.1 mmol, 0.10 equiv.) were placed in a flask with a magnetic stirring bar and a cooling column, and dissolved in 50 ml of acetone. The mixture was refluxed for 24 h. After cooling down, the mixture was filtered and concentrated in vacuo. The crude product was subjected to a column chromatography using CH2Cl2 to afford the product as pale yellow solid (10.3 g, 35.0 mmol, 87% yield). 1H NMR (400 MHz, CDCl3) δ: 9.85 (s, 1H), 7.83 (d, 2H, J=8.6 Hz), 7.00 (d, 2H, J=8.6 Hz), 4.05 (t, 2H, J=6.4 Hz), 1.80 (m, 2H), 1.27 (m, 18H), 0.89 (t, 3H, J=6.7 Hz); 13C NMR (500 MHz, CDCl3) δ: 191.0, 164.5, 132.2, 130.0, 115.0, 68.7, 32.2, 29.9, 29.8, 29.6, 29.3, 26.2, 22.9, 14.4; APCI-MS m/z 291.3 (M+).

Provenance & Evidence