Synthesis
To a suspension of acetone (50 mL) containing potassium carbonate (K2CO3, 20.7 g, 150 mmol) was sequentially added methyl 4-hydroxyphenylacetate (5.0 g, 30 mmol) and benzyl chloride (10.4 mL, 90 mmol). The reaction mixture was heated to reflux for 24 hours. Upon completion of the reaction, the mixture was cooled to room temperature, filtered to remove insoluble solids and the filtrate was concentrated. The residue was purified by silica gel column chromatography with 10% ethyl acetate/hexane as eluent to afford methyl 4-benzyloxyphenylacetate (7.7 g, 100% yield) as a white solid. Its 1H NMR (300 MHz, CDCl3) data were as follows: δ 7.40 (m, 5H), 7.21 (d, J = 6.6 Hz, 2H), 6.95 (d, J = 6.6 Hz, 2H), 5.05 (s, 2H), 3.70 (s, 3H), 3.59 (s, 2H).
References
[1] Patent: EP1218005, 2004, B1. Location in patent: Page 26
[2] Patent: WO2014/69963, 2014, A1. Location in patent: Paragraph 464-466
[3] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 4, p. 1209 - 1213
[4] Journal of Organic Chemistry, 1982, vol. 47, # 15, p. 2846 - 2851
[5] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 4, p. 525 - 528
