Synthesis
To a solution of N,N-dimethylformamide (80 mL) of 2-hydroxy-5-methoxybenzoic acid (6.0 g, 35.68 mmol) was sequentially added sodium bicarbonate (3.15 g, 37.46 mmol) and iodomethane (2.33 mL, 37.46 mmol). The reaction mixture was stirred at 80 °C for 3 hours. Upon completion of the reaction, ice water was added to the mixture, followed by extraction with ether. The combined organic phases were washed sequentially with water and saturated brine and then dried with anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure to give the brown oily product methyl 2-hydroxy-5-methoxybenzoate (5.38 g, 82.8% yield).
References
[1] Patent: US2004/242615, 2004, A1. Location in patent: Page/Page column 13
[2] ChemMedChem, 2016, vol. 11, # 1, p. 108 - 118
[3] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 2, p. 334 - 343
[4] Organic Letters, 2018, vol. 20, # 5, p. 1316 - 1319
