Synthesis of 4-ethyl-2-methoxyphenyl-icosanoate

4-ethylguaiacol (0.76 g, 5.0 mmol) and arachidic acid (1.72 g, 5.5 mmol) were allowed to react with presence of acetonitrile (25 mL, 0.5 mol), 4-(dimethylamino) pyridine (DMAP) (0.06 g, 0.5 mmol) and EDC.HCl (1.25 g, 6.5 mmol). The resulting mixture was stirred and heated at 92°C until the reaction completed as shown by the results from Thin-layer chromatography. The organic layer was separated by aqueous/organic workup, where hexane (20 mL), 1M aqueous HCl (2*20 mL), 10 wt% sodium bicarbonate (2*20 mL)were added separately to the mixture and the aqueous layer formed every time collected in a conical flask, washed by water (20 mL) and saturated sodium chloride (2×20 mL), dried (MgSO4), and evaporated to afford a colourless oil. This oil solidified under room temperature, turning into a white solid: 1.49 g (67%). M.P. 48.4 – 49.1 d = 6.94 (1H, d, J = 8.0 Hz), 6.80 (2H, m, 1J = 8.0 Hz, 2J=4.0 Hz), 3.82 (3H, s), 2.66 (2H, q, J = 8.0 Hz), 2.58 (2H, t, J = 6.0 Hz), 1.79 (2H, p, J = 8.0 Hz), 1.44 (4H, m), 1.34 (6H, J = 12.0 Hz), 1.30 (19H, s), 1.27 (6H, t), 0.92 (3H, t, J = 8.0 Hz). IR: v (cm-1) = 2955, 2915, 2870 and 2848 (s, CH), 1744 (s, C=O), 1510, 1469, 1450, 1411 (s, CO), 1335, 1304, 1270, 1241, 1227, 1200, 1146, 1118, 1104, 1035, 916, 896, 844, 718, 631, 541, 504, 466, 409.