Synthesis
2,4-Dihydroxybenzaldehyde (3.0 g, 1.0 eq.) was dissolved in acetonitrile (220 mL), sodium bicarbonate (2.2 eq.) was added at room temperature and stirred for 45 minutes. Subsequently, benzyl bromide (1.1 eq.) was slowly added to the reaction system. The reaction mixture was heated to reflux and stirred continuously. Upon completion of the reaction, the reaction was quenched with deionized water (100 mL) and subsequently extracted with ethyl acetate (3 x 25 mL). The organic phases were combined, washed with saturated saline (2 × 15 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to remove the solvent, to afford the crude product 4-phenylmethoxy-2-hydroxybenzaldehyde 12 as a white solid, which could be used in subsequent reactions without further purification.
References
[1] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 15, p. 4502 - 4510
[2] Synlett, 2011, # 11, p. 1605 - 1607
[3] Organic Process Research and Development, 2011, vol. 15, # 5, p. 1149 - 1162
[4] Tetrahedron Letters, 2013, vol. 54, # 31, p. 4121 - 4124
[5] Organic Letters, 2008, vol. 10, # 21, p. 5007 - 5010
