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Issue 4, 2012
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Highly regioselective di-tert-amylation of naphthalene over reusable H-mordenite zeolite

Keith Smith,*a  Alaa K. H. Al-Khalaf,a  Gamal A. El-Hiti*a  and  Samuel Pattissona 
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* Corresponding authors

a School of Chemistry, Cardiff University, Main Building, Park Place, Cardiff, UK
E-mail: smithk13@cardiff.ac.uk, el-hitiga@cardiff.ac.uk
Fax: +44(0)2920870600
Tel: +44(0)2920870600

Abstract

Highly regioselective di-tert-amylation of naphthalene using different alcohols can be achieved over a H-mordenite (HM) zeolite. For example, the tert-amylation of naphthalene using tert-amyl alcohol in cyclohexane over HM (Si/Al = 10) zeolite has been optimised to give a 70% yield of 2,6-dialkylnaphthalenes, of which 2,6-di-tert-amylnaphthalene was produced in 46% yield along with 2-tert-amyl-6-tert-butylnaphthalene (23%) and 2,6-di-tert-butylnaphthalene (1%). This has been achieved by varying the reaction time, temperature, pressure and amounts of tert-amyl alcohol and zeolite. No 2,7-dialkylnaphthalenes were seen under the conditions tried. The zeolites can be easily regenerated by heating and then reused.

Graphical abstract: Highly regioselective di-tert-amylation of naphthalene over reusable H-mordenite zeolite

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Publication details

The article was received on 11 Nov 2011, accepted on 31 Jan 2012 and first published on 29 Feb 2012


Article type: Paper
DOI: 10.1039/C2GC16443D
Citation: Green Chem., 2012,14, 1103-1110
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    Highly regioselective di-tert-amylation of naphthalene over reusable H-mordenite zeolite

    K. Smith, A. K. H. Al-Khalaf, G. A. El-Hiti and S. Pattisson, Green Chem., 2012, 14, 1103
    DOI: 10.1039/C2GC16443D

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