Synthesis
The general procedure for the synthesis of 2-ethoxybenzaldehyde from o-ethoxybenzyl alcohol was as follows: first, o-ethoxybenzyl alcohol (100 mg, 0.818 mmol), SS-Pd catalyst (918 mg, containing 0.04 mmol Pd), and 3 ml of toluene were mixed and the reaction mixture was purged with molecular oxygen. Subsequently, the reaction was stirred at 110 °C for 5 h, during which the reaction process was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the reaction mixture was cooled to room temperature, diluted with ethyl acetate and filtered through a cotton bed. The combined organic layers were concentrated by evaporation under reduced pressure and the crude product obtained was purified by silica gel (60-120 mesh) column chromatography (eluent was 95:5 hexane/ethanol solvent mixture) to give 2-ethoxybenzaldehyde (94 mg, 96% yield) as a colorless liquid.
References
[1] Tetrahedron Letters, 2001, vol. 42, # 31, p. 5199 - 5201
[2] Tetrahedron Letters, 2013, vol. 54, # 23, p. 2924 - 2928
[3] Tetrahedron Letters, 2011, vol. 52, # 38, p. 4954 - 4956
[4] Canadian Journal of Chemistry, 2008, vol. 86, # 8, p. 782 - 790
