Crystal structure of 2-acetyl-5-methoxyphenyl 2-(6-methoxynaphthalen-2-yl) propanoate, C23H22O5

Abstract

Source of material Naproxen (0.015 mol, 3.45 g) was dissolved in anhydrous methylene chloride (12 mL), and then oxalyl chloride (0.018 mol, 1.7 mL) and two drops of N, N-dimethylformamide was dropwise added at 0°C. The solution was stirred overnight at room temperature. After the solvent and excess oxalyl chloride was removed by vacuum distillation, the residue was washed three times with dry toluene to obtain a yellow solid, naproxen acylchloride. Paeonol, 1-(2-hydroxy-4-methoxyphenyl)-ethanone (0.01 mol, 1.66 g) and 4-(dimethylamino)-pyridin (DMAP, 0.0015 mol, 0.18 g) were dissolved in dry tetrahydrofuran (20 mL) and triethylamine (0.015 mol, 2 mL). To the solution a solution of naproxen acylchloride in dry tetrahydrofuran was dropwise added at 0°C. The reaction mixture was stirred for 5 h at room temperature. The reaction mixture was filtrated to remove the solid and the filtrate was concentrated under vacuum to remove the solvent. The residue was dissolved in methylene chloride, successively washed with 5% NaHCO 3 solution and water to pH = 7, and dried with anhydrous Na 2 SO 4 . The solution was filtrated, and concentrated under vacuum to obtain crude product. The crude product was purified by recrystallization in ethyl acetate. The single crystals were obtained from methanol solution. Experimental detailsAll the carbon-bounded H atoms were positioned geometrically with d(C-H) = 0.93-0.98 Å and U iso (H) = 1.2 or 1.5 U eq (C).