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Acylation of Alkyl 1,4-Dimethoxybenzenes By Substituted Benzoic Acids in Trifluoroacetic Acid‡

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A clean, convenient and highly selective acylation of alkyl 1,4-dimethoxy-benzenes, e.g., 2-methyl-1,4-dimethoxybenzene, by using substituted benzoic acids in dry trifluoroacetic acid has been achieved. The substituted benzophenones were found to be the sole product and their formation could be much reduced or even completely inhibited by adding a small amount of water. Kinetic studies show that the reaction obeys second-order kinetics with rate = k2.[substrate][ArCO2H]. The very negative reaction constant (p =- 6.43) derived from the excellent Hammett correlation (r = 0.99) reveals that electron-donating substituents in benzoic acid strongly favour the protonation of the acid by trifluoroacetic acid, increasing the concentration of the acylating agents, ArC+=O, and thus lead to the effective aromatic acylation.

Affiliations: 1: Department of Chemistry Huazhong University of Science and Technology Wuhan 430074, China


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