Synthesis
The reaction was carried out with methyl 3,5-dihydroxybenzoate (104 g) and iodomethane (36 mL) in the presence of potassium carbonate (79 g) and dimethylformamide (1200 mL) with stirring at room temperature for 16 hours. After completion of the reaction, the reaction mixture was partitioned between water (2.5 L) and petroleum ether (boiling point 60-80 °C, 600 mL). The aqueous layer was washed with petroleum ether (boiling point 60-80 °C, 600 mL) and then extracted with toluene (2 x 1 L). The toluene extracts were combined, washed sequentially with water (4×800 mL), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give methyl 3-hydroxy-5-methoxybenzoate as an oil (33 g, 30% yield).
References
[1] Synlett, 2016, vol. 27, # 10, p. 1587 - 1591
[2] European Journal of Medicinal Chemistry, 2013, vol. 63, p. 415 - 422
[3] Journal of the American Chemical Society, 2005, vol. 127, # 6, p. 1737 - 1743
[4] Journal of Organic Chemistry, 2013, vol. 78, # 11, p. 5587 - 5603
[5] Synlett, 2006, # 9, p. 1363 - 1366
