Synthesis
4-Hydroxy-2-methoxybenzaldehyde (200 mg, 1.31 mmol) was dissolved in N,N-dimethylformamide (DMF) under the protection of nitrogen (N2), potassium carbonate (K2CO3, 543 mg, 3.93 mmol) was added, and stirred for 30 min at room temperature. Subsequently, benzyl bromide (BnBr, 0.312 mL, 2.62 mmol) was added dropwise to the reaction mixture and stirring was continued for 1.5 hours. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (EtOAc) and washed with deionized water (H2O). The organic phase was dried with anhydrous sodium sulfate (Na2SO4) and concentrated under reduced pressure. Purification by silica gel column chromatography with ethyl acetate/hexane (1:2, v/v) as eluent afforded the target product 4-benzyloxy-2-methoxybenzaldehyde (304 mg, 95.7% yield).1H-NMR (CDCl3, 400 MHz) δ: 7.81 (d, 1H, J = 8.6 Hz), 7.36 (m, 5H), 6.62 ( dd, 1H, J = 8.7, 2.2 Hz), 6.54 (d, 1H, J = 2.2 Hz), 5.14 (s, 2H), 3.89 (s, 3H).
References
[1] Molecules, 2015, vol. 20, # 9, p. 15966 - 15975
[2] Bioorganic and Medicinal Chemistry, 1998, vol. 6, # 9, p. 1429 - 1437
[3] Journal of the American Chemical Society, 2006, vol. 128, # 33, p. 10640 - 10641
[4] Patent: WO2006/40520, 2006, A1. Location in patent: Page/Page column 103
[5] Patent: WO2007/99326, 2007, A1. Location in patent: Page/Page column 111
