Synthesis
General method: A mixture of 4-hydroxy-1-naphthaldehyde (1 eq.), potassium carbonate (K2CO3, 1.5 eq.) and iodomethane (1.5 eq.) in acetone (12 mL/mmol) was stirred under reflux conditions for 4 to 24 hours. The progress of the reaction was monitored by thin layer chromatography (TLC) until complete disappearance of the raw material. Upon completion of the reaction, the solvent was removed by evaporation under reduced pressure. The residue was purified by silica gel column chromatography with an eluent ratio of cyclohexane/ethyl acetate (90:10 to 70:30).
References
[1] Physical Chemistry Chemical Physics, 2015, vol. 17, # 15, p. 10238 - 10249
[2] European Journal of Medicinal Chemistry, 2016, vol. 123, p. 161 - 170
[3] Justus Liebigs Annalen der Chemie, 1907, vol. 357, p. 373
[4] Journal of the American Chemical Society, 1982, vol. 104, # 16, p. 4469 - 4477
[5] Journal of Medicinal Chemistry, 2012, vol. 55, # 20, p. 8969 - 8973
