Sodium Hydroxide → 3-(1-(4-Fluorophenyl)cyclohexyl)propanoic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 3-(1-(4-fluorophenyl)cyclohexyl)propanoate (Intermediate 7, 1.347 g, 4.84 mmol) in methanol (20 mL) was added 1N sodium hydroxide (9.68 mL, 9.68 mmol), and the mixture was stirred at 60° C. for 7 hrs. After cooling, methanol was evaporated off and the residue was acidified with 12 mL of 1N HCl. The product was extracted with ethyl acetate (2×) and the combined extracts were washed with brine, dried over sodium sulfate and evaporated to give the desired 3-(1-(4-fluorophenyl)cyclohexyl)propanoic acid (1.183 g, 4.73 mmol, 98% yield) as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 7.26 (2H, dd, J=8.80, 5.28 Hz), 7.01 (2H, t, J=8.69 Hz), 2.01-2.10 (2H, m), 1.95-2.01 (2H, m), 1.82-1.88 (2H, m), 1.31-1.62 (8H, m).

Provenance & Evidence