Synthesis
2-Benzoyloxy-5-methylacetophenone (I) (5 g, 19.6 mmol) was reacted with 15 g of powdered hot KOH in 25 ml of pyridine and heated at 100 °C for 30 min. After completion of the reaction, the reaction mixture was slowly poured into pre-cooled and acidified (6N HCl) ice water. Subsequently, the precipitated yellow precipitate was collected by filtration. The resulting solid residue was dried under vacuum. The crude product 1-(2-hydroxy-5-methylphenyl)-3-phenylpropane-1,3-dione (II) was purified by recrystallization from petroleum ether, resulting in yellow bright plate-like crystals. Yield: 75%; mass of isolated product: 3.73 g; melting point: 95 °C (literature value: 94 °C [34]).
References
[1] Journal of the Indian Chemical Society, 2006, vol. 83, # 8, p. 835 - 837
[2] European Journal of Medicinal Chemistry, 2014, vol. 73, p. 195 - 209
[3] Chemistry Letters, 2007, vol. 36, # 4, p. 522 - 523
[4] Journal of Organic Chemistry, 1991, vol. 56, # 26, p. 7292 - 7297
[5] Journal of the Indian Chemical Society, 1986, vol. 63, p. 851 - 853
