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Acylation of alkll 1,4-dimethoxybenzenes by substituted benzoic acids in trifluoroacetic acid

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Abstract

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, ArtC+=0, and thus lead to the effective aromatic acylation.

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Authors and Affiliations

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

    Yue-Fa Gong, Cheng-Xue Zhao & Hong Pen

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  1. Yue-Fa Gong
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  2. Cheng-Xue Zhao
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  3. Hong Pen
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Additional information

This manuscript is published as part of a series of papers dedicated to Professor You-Cheng Liu on the occasion of his 70th birthday. This series of articles was edited by Professor Zhong-Li Liu, Lanzhou University, Lanzhou, China.

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Gong, YF., Zhao, CX. & Pen, H. Acylation of alkll 1,4-dimethoxybenzenes by substituted benzoic acids in trifluoroacetic acid. Res Chem Intermed 14, 161–169 (1990). https://doi.org/10.1163/156856790X00238

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  • DOI: https://doi.org/10.1163/156856790X00238

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