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Updated: Jun 13, 2025
Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Insights into the Mechanism of 2-Methylnaphthalene Friedel-Crafts Acetylation Catalyzed by AlCl3: A Combined
Fanyuan Zhang1, Youcai Zhu1, Jiongyi Chen1
1School of Chemical Engineering, East China University of Science and Technology, Shanghai 200237, China.
Abstract:
The Friedel-Crafts acetylation of 2-methylnaphthalene (2-MN) represents a powerful approach for synthesizing 2-methyl-6-acetylnaphthalene (2,6-MAN). The identification of catalytically active species in Friedel-Crafts acylation has recently attracted considerable attention. In this study, we performed an experimental and computational investigation of the AlCl3-catalyzed Friedel-Crafts acetylation of 2-MN in nitrobenzene and dichloromethane solvents. The yield of the acetylation can be significantly affected by the solvent and the addition method. Following the substitution mechanism, the stepwise deprotonation pathway is preferred in both solvents, which is mediated by the donor-acceptor complex as the catalytically active species. The calculations with the explicit solvent led to the same conclusions. This study provides important understanding of the AlCl3-catalyzed Friedel-Crafts acetylation reaction, with potential applications to other Lewis acid-catalyzed acylation reactions.
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