5-formyl-2-methoxyphenyl cyclohexanecarboxylate

Isovanillin (0.005 mol, 0.7 g) was added to cyclohexanecarboxylic acid (0.0055 mol, 0.8 g) and dissolved in 34 mL acetonitrile with 1.1 g EDC.HCl and 0.0611 g DMAP. Reaction flask was heated under reflux for one hour. 20 mL hexane was added to mixture, then washed with 1 M aqueous HCl 20 mL x2, 10%wt aqueous sodium bicarbonate 20 mL x2, distilled water 20 mL x1, brine 20 mL x2, and dried using MgSO4. Mixture was filtered under gravity and solvent removed by rotary evaporation. Further workup was performed on aqueous layer by extraction into 70 mL ethyl acetate, washing with brine 20 mL, drying with MgSO4 and solvent removal by rotary evaporation. Product was a white, crystalline solid: 0.8 g (61.1%). 1H NMR (400 MHz, CDCl3): δ = 9.85 (s, 1H, CHO), 7.735 (dd, 1H, 3J = 8.5 Hz, 4J = 2.0 Hz, Ar-H), 7.555 (d, 1H, 4J = 2.0 Hz, Ar-H), 7.055 (d, 1H, 3J = 8.5 Hz, Ar-H), 3.89 (s, 3H, OCH3); IR (ATR): ν (cm-1) = 2937 (C-H), 2917, 2849, 1749, 1676 (C=O), 1605, 1578, 1509, 1457, 1438, 1392, 1331, 1318, 1278, 1258, 1206, 1182, 1162, 1117, 1098, 1065, 1020, 979, 961, 922, 896, 878, 826, 801, 788, 725, 669, 635, 587, 573, 558, 532, 520, 472, 440, 419, 410.