4-acetyl-2-methoxyphenyl 4-methylcyclohexane-1-carboxylate

4-dimethylaminopyridine(DMAP) (0.1 g, 0.5 mmol) and EDC.HCl (1.2 g, 6.5 mmol) were added to acetonitrile(15 mL). trans-4-methyl-1-cyclohexanecarboxylic acid (0.7 g, 5 mmol, in 8 mL acetonitrile) and acetovanillinone (0.8 g, 5 mmol, in 10.5 mL acetonitrile) were added to the resultant mixture. The mixture was heated under reflux and the progress of the reaction was monitored by thin layer chromatography. After refluxing for 2.5 h, hexane (20 mL) was added and the resultant mixture was washed with 1M hydrochloric acid (2 x 20 mL). As white precipitate was observed, the mixture was washed with 10 mL ethyl acetate, before washing with 10 wt% sodium bicarbonate (2 x 20 mL) and subsequently with 20 mL distilled water. As white precipitate was observed once more, the resultant mixture was washed with 20 mL ethyl acetate before washing with saturated aqueous sodium chloride (2 x 20 mL). The separated organic phase was dried (MgSO4) and filtered under gravity. MgSO4 was rinsed with 10 mL ethyl acetate and the rinsings were transferred to the filtrate. Volatiles were removed in vacuo to give a white powder (1.0 g, 3.4 mmol, 67% yield). 1H NMR (400 MHz, CDCl3) δH 7.57 (1H, d, J = 2.0 Hz), 7.53 (1H, dd, J = 2.0, 8.0 Hz), 7.08 (1H, d, J = 8.4 Hz), 3.85 (3H, s), 2.58 (3H, s), 2.50 (1H, tt, J = 3.2, 12.4 Hz), 2.13 (2H, dd, J = 2.8, 14.4 Hz), 1.80 (2H, dd, J = 3.2, 14.0 Hz), 1.55 (4H, td, J = 3.2, 12.4 Hz), 1.43 - 1.36 (1H, m), 1.00 (2H, qd, J = 3.2, 13.2 Hz), 0.91 (3H, d, J = 6.8 Hz) ppm; IR (ATR, neat) νmax/cm-1 1751 (s, C=O), 1122 (s, C-O)