Synthesis
The general procedure for the synthesis of 2-hydroxy-5-methylacetophenone from p-cresyl acetate was as follows: p-tolyl acetate (10 g, 0.067 mol) and aluminum chloride (10.7 g, 0.08 mol) were added to a 500-mL round-bottomed flask. The reaction mixture was heated in an oil bath at 140-150°C for 5-6 hours. The reaction process was monitored by thin layer chromatography (TLC) using ethyl acetate:hexane as the unfolding agent. After completion of the reaction, the reaction mixture was quenched with crushed ice and the resulting solid product was extracted with ethyl acetate (2 x 50 mL). The organic phase was washed with brine solution (2 x 15 mL) and dried with anhydrous sodium sulfate. Subsequently, the solvent was removed by distillation under reduced pressure to give the crude product. The crude product was purified by aqueous ethanol recrystallization to afford the target compound 2-hydroxy-5-methylacetophenone in 92% yield with a melting point of 45-48°C.
References
[1] Journal of Organic Chemistry, 1981, vol. 46, p. 4971 - 4975
[2] Journal of Chemical Research, Miniprint, 2003, # 12, p. 1258 - 1270
[3] Journal of Chemical Research, Synopses, 1999, # 9, p. 574 - 575
[4] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996, vol. 35, # 7, p. 734 - 736
[5] Journal of Chemical Research, Miniprint, 1998, # 10, p. 2678 - 2695
