Synthesis
The general procedure for the synthesis of phenylmethyl ethanoate from ethanoic acid and benzyl bromide was as follows: first, a suspension formed by 2-hydroxyacetic acid (70% aqueous solution, 889 mg, 12.0 mmol) and Cs2CO3 (1955 mg, 6.00 mmol) in a solvent mixture of methanol (22 mL) and water (4 mL) was stirred for 30 min at room temperature. Subsequently, the solvent was removed and the residue was dissolved in DMF (18 mL) pre-cooled to 0 °C. After 10 min, benzyl bromide (2155 mg, 12.6 mmol) was added and the reaction mixture was continued to be stirred for 24 h at room temperature. Upon completion of the reaction, the reaction was quenched with brine (20 mL) and the organic layer was extracted with ethyl acetate (3 x 25 mL). The extract was washed sequentially with water (25 mL) and brine (20 mL), dried over MgSO4 and concentrated in vacuum to afford 1877 mg (97% yield) of benzyl 2-hydroxyacetate as a colorless liquid.HPLC analysis showed a retention time of 2.68 min (70%).
References
[1] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 16, p. 4903 - 4909
[2] Journal of Organic Chemistry, 2000, vol. 65, # 22, p. 7667 - 7675
[3] Patent: US2016/340365, 2016, A1. Location in patent: Paragraph 0126; 0127
[4] Patent: US2016/297784, 2016, A1. Location in patent: Paragraph 0150; 0151
[5] Journal of the American Chemical Society, 2010, vol. 132, # 31, p. 10920 - 10934
