4-ethylphenyl docosanoate

4-dimethylaminopyridine (0.06 g, 0.49 mmol), EDC.HCl (1.24 g, 6.47 mmol), behenic acid (1.74 g, 5.11 mmol), and 4-ethylphenol (0.62 g, 5.08 mmol) were dissolved in acetonitrile (33 mL, excess) and heated to 95 °C under reflux for 40 minutes to give a white solid at the bottom of the resulting solution once cooled to room temperature. Added hexane (20 mL, excess) to solution and dissolved the solid back into solution at 50 °C. Washed twice with 1 M aqueous HCl (2 x 20 mL), twice with 10 % wt. sodium bicarbonate (2 x 20 mL), and with distilled water (20 mL). The organic phase was separated, dried twice with brine (2 x 22 mL) and MgSO4, and evaporated to afford the desired product as a white powdery solid (1.18 g, 2.65 mmol, 52.2 % yield). M.p. 52.9 – 54.3 °C