Uses
2'',3''-Dimethoxyacetophenone is used as a reactant in the preparation and antileishmanial activity of quinazolinone hybrids.
Preparation
Obtained by heating its oxime with pyridinium chloride containing 5% of water (35%).
Synthesis
General procedure for the synthesis of 2,3-dimethoxyacetophenone from 1-(2,3-dimethoxyphenyl)ethanol: Potassium dichromate (24.76 g), water (124 mL), and concentrated sulfuric acid (12 mL) were prepared into a solution, and 1-(2,3-dimethoxyphenyl)ethanol (10.06 g, 55.3 mmol) was added, and the reaction was stirred for 15 min at room temperature. After completion of the reaction, the reaction mixture was extracted with ether and the organic phase was washed sequentially with 5% potassium carbonate solution (2 x 150 mL) and saturated sodium chloride solution (1 x 100 mL). The organic phase was dried and the solvent was evaporated under reduced pressure to obtain the crude product. The crude product was purified by high-vacuum distillation and collected at a pressure of 0.3 Torr and a temperature of 85 °C to give 6.47 g of 2,3-dimethoxyacetophenone in 65% yield. The 1H NMR (300 MHz, CDCl3) data of the product were as follows: δ 2.62 (s, 3H), 3.88 (s, 3H), 3.90 (s, 3H), 7.05-7.10 (m, 2H), 7.21 (dd, 1H).
References
[1] Patent: US5990142, 1999, A
[2] Journal of the American Chemical Society, 1951, vol. 73, p. 793
[3] Chemische Berichte, 1913, vol. 46, p. 4019
[4] Journal of the American Chemical Society, 2005, vol. 127, # 29, p. 10371 - 10387
