Synthesis
Example 1 Synthesis of 3-benzyloxyacetophenone: 1 kg (7.35 mol) of 3-hydroxyacetophenone, 1.035 kg (7.5 mol) of anhydrous potassium carbonate, and 0.945 kg (7.5 mol) of benzyl chloride were dissolved in 4.1 L of acetone with mechanical stirring and heated and refluxed for 24 hrs. Subsequently, 0.1035 kg (0.75 mol) of anhydrous potassium carbonate and 0.0945 kg (0.75 mol) of benzyl chloride were added and refluxing was continued. the above additions were repeated after 72 hours and refluxing was continued to a total reaction time of 96 hours. After completion of the reaction, the reaction mixture was cooled, filtered and the filtrate was concentrated by rotary evaporator. To the concentrated filtrate was added 0.202 kg (2.0 mol) of triethylamine and stirred overnight. The reaction mixture was diluted with 1 L of ether and filtered, the filtrate was concentrated by evaporation and the residue was distilled to give 1.429 kg (86% yield) of the target product 3-benzyloxyacetophenone as an oil. Boiling point: 160°C (0.3 Torr).IR (CHCl3) spectrum showed absorption peaks located at 1695, 1605, 1595, 1493 and 1433 cm-1 .PMR (CDCl3) spectrum showed chemical shifts δ 2.52 (s, CH3), 5.03 (s, CH2) and 7.0-7.7 (m, Ph).
References
[1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1988, p. 2491 - 2500
[2] Journal of Medicinal Chemistry, 1992, vol. 35, # 16, p. 3045 - 3049
[3] Tetrahedron Letters, 2007, vol. 48, # 26, p. 4627 - 4630
[4] Chemical and Pharmaceutical Bulletin, 1995, vol. 43, # 5, p. 738 - 747
[5] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 5, p. 1537 - 1544
