1. In a 100 mL round bottom flask with a stirrer fitted with a three-way stopper, methanol (25 mL) and acetyl chloride (5.0 mL) were added and stirred to unsaturation.
2. HCl/MeOH solution was added slowly followed by methyl 2-hydroxyphenylacetate (5.00 g, 32.9 mmol) and the reaction was stirred at room temperature for 20 hours.
3. After completion of the reaction, the reaction endpoint was confirmed by TLC and 1H-NMR, and methanol was removed by distillation under reduced pressure.
4. The reaction mixture was neutralized with NaHCO3 solution (10 mL) and subsequently extracted with ether and distilled under reduced pressure to obtain the crude product.
5. The crude product was transferred to a 200 mL round-bottomed flask, K2CO3 (80 g, 34.8 mmol) and DMF (60 mL) were added, and a three-way stopper and stirrer were fitted.
6. BnBr (5.85 g, 34.2 mmol) and DMF (15 mL) were added in a dropping funnel and slowly added dropwise to the reaction flask and the reaction was carried out for 10 h at room temperature.
7. After completion of the reaction, water (15 mL) was added, extracted with ether, the organic phase was dried with Na2SO4 and distilled under reduced pressure to give methyl 2-(2-(benzyloxy)phenyl)acetate.
[1] Patent: JP5690514, 2015, B2. Location in patent: Paragraph 0068
[2] Patent: US5374644, 1994, A
[3] Patent: US4870075, 1989, A
[4] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 2, p. 131 - 134
[5] Synlett, 2018, vol. 29, # 17, p. 2265 - 2268
