Synthesis
General procedure for the synthesis of 4-(2-hydroxyethyl)benzoic acid from methyl 4-(2-hydroxyethyl)benzoate: sodium hydroxide (58 mg, 1.43 mmol) was added to a mixed solution of methanol (3 mL) and water (1 mL) of methyl 4-(2-hydroxyethyl)benzoate (174 mg, 0.96 mmol) at room temperature. The reaction mixture was stirred at room temperature for 48 hours. Upon completion of the reaction, water (5 mL) was added to dilute and extracted with ether (3 x 20 mL) to remove unreacted feedstock and by-products. The aqueous phase was acidified with a 1:1 hydrochloric acid solution to pH=1 and a white solid was precipitated. The solid was collected by filtration to afford 4-(2-hydroxyethyl)benzoic acid (158 mg, 100% yield), and the product could be used in the next reaction without further purification. The structure of the product was confirmed by 1H NMR (300 MHz, CDCl3): δ 7.97 (d, J = 8.4 Hz, 2H), 7.27 (d, J = 8.4 Hz, 2H), 3.83 (t, J = 6.3 Hz, 2H), 2.88 (t, J = 6.3 Hz, 2H).
References
[1] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 11, p. 2988 - 2998
[2] Journal of the American Chemical Society, 2006, vol. 128, # 50, p. 16020 - 16021
