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Issue 13, 2003
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Acylation of aromatic ethers over solid acid catalysts: scope of the reaction with more complex acylating agents

Keith Smith,*a  Gamal A. El-Hiti,a  Anthony J. Jaynea  and  Michael Buttersb 
Author affiliations

* Corresponding authors

a Centre for Clean Chemistry, Department of Chemistry, University of Wales Swansea, Singleton Park, UK

b AstraZeneca, Global Process R&D, Avlon Works, UK

Abstract

Acylation of anisole with 2-phenylbutanoic acid derivatives, over zeolite catalysts, gives the corresponding 4-acyl derivatives with high regioselectivity. In an analogous way, 2,3-dihydrobenzofuran reacts with acid anhydrides or chlorides in the presence of catalytic quantities of zeolites to give the corresponding 5-acyl-2,3-dihydrobenzofurans. The zeolite can be recovered, regenerated and used again to give almost the same yield as with fresh zeolite. The reaction has been applied to the synthesis of ethyl (2,3-dihydrobenzofuran-5-yl)glyoxylate.

Graphical abstract: Acylation of aromatic ethers over solid acid catalysts: scope of the reaction with more complex acylating agents

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Publication details

The article was received on 10 Apr 2003, accepted on 13 May 2003 and first published on 28 May 2003


Article type: Paper
DOI: 10.1039/B303906D
Citation: Org. Biomol. Chem., 2003,1, 2321-2325
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    Acylation of aromatic ethers over solid acid catalysts: scope of the reaction with more complex acylating agents

    K. Smith, G. A. El-Hiti, A. J. Jayne and M. Butters, Org. Biomol. Chem., 2003, 1, 2321
    DOI: 10.1039/B303906D

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