Methanol → Methyl trans-4-(4-chlorophenyl)cyclohexanecarboxylate

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Reaction Steps

To a stirred solution of the 4-(4-chlorophenyl)cyclohexanecarboxylic acid (0.5 g, 2.095 mmol) in methanol (10 mL) was added one drop of conc. sulfuric acid. After stirring overnight at room temperature, the reaction mixture was extracted with ethyl acetate and washed with water, saturated sodium bicarbonate and brine. It was then dried over anhyd. magnesium sulfate, concentrated and dried in vacuo to yield methyl 4-(4-chlorophenyl)cyclohexanecarboxylate a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 7.23-7.30 (2H, m), 7.10-7.17 (2H, m), 3.70 (3H, s), 2.44-2.56 (1H, m), 2.36 (1H, tt, J=12.13, 3.60 Hz), 2.07-2.16 (2H, m), 1.92-2.01 (2H, m), 1.38-1.67 (4H, m).

Provenance & Evidence