Synthesis
Ethyl 2-hydroxy-6-methylbenzoate (1.0 g, 5.6 mmol), iodomethane (866 mg, 6.1 mmol), and potassium carbonate (1.5 g, 11.1 mmol) were dissolved in acetone (20 mL) and the reaction was heated to reflux for 17 hours. Upon completion of the reaction, the reaction was quenched by adding water (20 mL) to the reaction mixture and extracted with dichloromethane (3 × 20 mL). The organic layers were combined, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure to remove the solvent. The crude product was purified by silica gel column chromatography (eluent: 100% hexane) to afford ethyl 2-methoxy-6-methylbenzoate (1.1 g, 99% yield) as a colorless oil.
References
[1] Tetrahedron, 1991, vol. 47, # 40, p. 8635 - 8652
[2] Patent: KR101777971, 2017, B1. Location in patent: Paragraph 0138-0139
[3] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1986, vol. 25, p. 796 - 798
