2-(3-(methoxycarbonyl)phenyl)acetic acid

52787-20-9

52787-19-6

Methyl 3-(methoxycarbonyl)benzoate 76 (500 mg, 2.40 mmol) was used as a raw material and dissolved in methanol (10 mL). To this solution was added a solution of K2CO3 (700 mg, 5.07 mmol) in water (10 mL) and the reaction was stirred overnight at room temperature. Upon completion of the reaction, the reaction mixture was concentrated and dissolved in water (20 mL). Subsequently, the unreacted diester 76 was extracted with water and EtOAc, and the aqueous phase was acidified with 1N HCl and then extracted with EtOAc (30 mL x 2). The organic layers were combined, dried with anhydrous sodium sulfate and concentrated in vacuum. The crude product was purified by silica gel column chromatography (eluent: hexane/EtOAc, 5:1) to afford the target product 2-(3-(methoxycarbonyl)phenyl)acetic acid 77 (508 mg, 90% yield). The product was detected by TLC (Rf = 0.36), 1H NMR (400 MHz, methanol-d4) δ 7.97 (d, J = 1.7 Hz, 1H), 7.91 (dt, J = 7.8,1.4 Hz, 1H), 7.57-7.49 (m, 1H), 7.43 (t, J = 7.6 Hz, 1H), 3.91 (s, 3H), and 3.67 (s, 2H); mass spectral analysis showed [M + H]+ = 195.14 (APCI+).