Sodium Hydroxide → 2-(3-methoxyphenyl)benzoic Acid

Participants

Reaction Steps

To a stirred solution of ethyl 2-(3-methoxyphenyl)benzoate from Step A (7.33 g, 28.6 mmol) in MeOH (200 mL) and water (30 mL) was added 1.0 N aq. NaOH (63 mL, 63 mmol) dropwise. The mixture was heated to reflux for 3 hours, then allowed to cool overnight. The solution was concentrated to remove most of the MeOH, cooled on ice, and 10% aq. citric acid (300 mL) was added. The resulting mixture was extracted with CH2Cl2 (3×250 mL), and the combined organic extracts were dried over Na2SO4, filtered, and concentrated under reduced pressure to give the titled product as a white solid.

Provenance & Evidence