Synthesis
Potassium carbonate (4.002 g, 29 mmol) and methyl gallate (6 g, 29.7 mmol) were dissolved in anhydrous dichloromethane followed by the addition of diiodomethane (2.8 mL, 34.8 mmol) under nitrogen atmosphere and at room temperature. The reaction mixture was stirred at 0 °C for 5 h and then warmed up to 120 °C to continue the reaction. Upon completion of the reaction, the mixture was poured into cooled water (500 mL) and extracted with ethyl acetate. The organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (eluent: 15% ethyl acetate/hexane) to afford the target product methyl 7-hydroxybenzo[d][1,3]meso-dioxole-5-carboxylate (3.6 g, 58% yield) as a white amorphous powder.
References
[1] Tetrahedron Asymmetry, 2009, vol. 20, # 4, p. 440 - 448
[2] Synlett, 2018, vol. 29, # 7, p. 908 - 911
[3] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 7, p. 2297 - 2298
[4] Liebigs Annalen der Chemie, 1994, # 4, p. 361 - 364
[5] Synthesis, 2009, # 20, p. 3383 - 3390
