By Satori G., Maggi R.
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Extra info for Advances in Friedel-Crafts Acylation Reactions.. Catalytic and Green Processes
33. Valters, R. E. and Flitsch, W. 1985. Ring‑chain tautomerism, ed. Katritzky, A. R. New York: Plenum Press. 34. , and Foglio, F. 1990. A new methodological approach to anthraquinone and antrhacyclinone synthesis. Gazz. Chim. Ital. 120: 13–19. 35. , and Pellinghelli, M. A. 1995. An investigation of the reaction mechanism of the bis‑acylation of aromatics with o‑phthaloyl dichlorides: regioselective synthesis of anthraquinones. J. Org. Chem. 60: 6588–6591. 36. , and Robles, P. 1987. Metal template ortho‑ acylation of phenols; a new general approach to anthracyclinones.
06), respectively. The catalyst can be recovered by precipitation with hexane from the final reaction mixture and reused in the benzoylation of meta‑xylene, giving the product with unchanged yield (∼95%) for four successive cycles. 30 By removing water from the reaction mixture by azeotropic distillation and adsorption onto molecular sieves, the yield of benzoylation of para‑xylene with BAC in the presence of perfluorobutanesulfonic acid (10% mol) is improved to 90%. 3). Better results are achieved by using phthaloyl dichloride under triflic acid catalysis (5% mol) at the same temperature: anthraqui‑ none 17 can be synthesized in 52% yield.
10). The method is also applied to the synthesis of 1‑tetralones and 1‑benzosuberones. 04. The reaction can be extended to different methoxyarenes and mesi‑ tylene with different aliphatic and aromatic acyl chlorides and anhydrides (48%–91% yield). 51 Since the acylium ion is much smaller than the adduct, attack at the steri‑ cally more hindered position can occur. 04 for all runs. The lowering of the catalyst efficiency is assumed to be due to the production of hydrogen chloride, possibly leading to the formation of an increasing amount of copper dichloride, which is inactive under these conditions.