4-formyl-2-methoxyphenyl tridecanoate

Tricadenoic acid (1.2 g, 5.5 mmol) and acetovanillinone (0.8 g, 5 mmol) were mixed with DMAP 4-(dimethylamino)pyridine (0.06 g, 0.5 mmol) and EDC.HCL (1.25 g, 6.5 mmol). The white solid mixture was dissolved in acetonitrile (30 mL) and became colourless oil. The reaction mixture was stirred and heated under reflux at around 90 °C for 85 minutes, during which, four samples were taken at a 20-minute interval for Thin Layer Chromatography to monitor the reaction progress. After allowing to cool to room temperature, the reaction mixture undergone extraction with hexane (20 mL) before washing accordingly with hydrochloric acid (2x 20 mL, 1M), sodium bicarbonate (2x 20 mL, 10 wt%), distilled water (1x 20 mL) and saturated aqueous sodium chloride (2x 20 mL). The remaining organic layer was then dried with magnesium sulfate in excess before filtering under gravity. The product was then isolated by removing solvent with a rotary evaporator at room temperature. This resulted in a colourless oil of isolated product as 4-acetyl-2-methoxyphenyl tridecanoate (1.0 g, 2.76 mmol, 55.2 % yield), which gradually crystallised into a white solid. M.P. 46.3 - 47.2 °C; 1H NMR (400 MHz, CDCl3) δH 7.73 – 7.45 (1H, m), 7.25 (1H, s) 7.09 (1H, d, J = 8.2 Hz), 3.87 (s, 1H), 2.95 – 2.35 (m, 3H), 1.75 (p, J = 7.4 Hz, 1H), 1.26 (d, J = 5.3 Hz, 6H), 1.26 (d, J = 5.3 Hz, 6H) ppm; IR (ATR, neat) νmax/cm-1 2970 and 2955 (w, CH2 & CH3), 2913 and 2849 (s, CH2 & CH3), 1762 and 1671 (s, C=O), 1584 and 1506 (m)