Sodium Hydroxide → 5-Chloro-2-fluoro-4-methylbenzoic acid

Participants

Reaction Steps

To a stirred solution of methyl 5-chloro-2-fluoro-4-methylbenzoate (Preparation 12, 340 mg, 1.68 mmol) in dioxane/water (5:1, 12 mL) was added a sodium hydroxide solution (5 M, 1.63 mL, 8.39 mmol). The reaction mixture was stirred at room temperature for 18 hours and then evaporated in vacuo. The resulting residue was suspended in water and extracted with diethyl ether (3×20 mL). The aqueous layer was separated, cooled in an ice bath, acidified with aqueous hydrochloric acid (6 M) and then extracted with EtOAc (30 mL). The combined organics were washed with brine (2×20 mL), dried over sodium sulphate, filtered and evaporated in vacuo to yield the title compound as a white solid (266 mg, 84%).

Provenance & Evidence