Synthesis
Benzyl bromide (4.4 g, 25.7 mmol) was added dropwise to a stirred solution of methyl 3,4,5-trihydroxybenzoate (0.94 g, 5.15 mmol) and potassium carbonate (6.56 g, 25.7 mmol) in N,N-dimethylformamide (DMF, 20 mL). The reaction mixture was stirred under nitrogen (N2) protection in an oil bath at 60 °C for 15 hours. Upon completion of the reaction, the reaction was quenched by adding an appropriate amount of water to the mixture and extracted with chloroform (3 × 20 mL). The organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford methyl 3,4,5-tris(benzyloxy)benzoate (1.93 g, 90% yield) as a white solid.
References
[1] Patent: EP1870403, 2007, A1. Location in patent: Page/Page column 95
[2] Patent: US2004/110790, 2004, A1. Location in patent: Page 14
[3] Bioscience, Biotechnology and Biochemistry, 2003, vol. 67, # 12, p. 2584 - 2590
[4] Patent: US7288273, 2007, B1. Location in patent: Page/Page column 38
[5] Synthetic Communications, 2002, vol. 32, # 20, p. 3149 - 3158
