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Issue 46, 2012
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Selective synthesis of 6,8-di-t-butylated flavan over Zn–Al containing mesoporous silica catalysts

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Abstract

We demonstrate a much green synthesis method for highly selective synthesis of 6,8-di-t-butylated flavan (6,8-DTBF) by liquid phase alkylation of 2,4-di-t-butylphenol (2,4-DTBP) with cinnamyl alcohol (Cin-OH) over mesoporous Zn–Al–MCM-41 catalysts synthesized under direct basic hydrothermal method. The main alkylated product, 6,8-DTBF is importantly used as an intermediate in the manufacture of biosynthetic organic compounds. The recyclable mesoporous Zn–Al–MCM-41 catalysts have also been reused in this reaction to study their catalytic activities. The influences of various reaction parameters such as temperature, time, ratios of reactant (2,4-DTBP-to-Cin-OH) have been extensively investigated for the synthesis of 6,8-DTBF. In addition, dimethyl sulfoxide (DMSO) has also been used as a solvent in this catalytic reaction. The mesoporous Zn–Al–MCM-41(75) gives excellent catalytic activity with 6,8-DTBF selectivity (86.0%) and 2,4-DTBP conversion (63.1%), and these catalytic results have also compared with that obtained using other mesoporous and microporous catalysts. On the basis of catalytic activity obtained by using the all catalysts, the Zn–Al–MCM-41(75) catalyst is found to be a highly active, recyclable and eco-friendly heterogeneous catalyst in the liquid-phase alkylation of 2,4-DTBP.

Graphical abstract: Selective synthesis of 6,8-di-t-butylated flavan over Zn–Al containing mesoporous silica catalysts

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Publication details

The article was received on 29 Jun 2012, accepted on 28 Aug 2012 and first published on 09 Oct 2012


Article type: Paper
DOI: 10.1039/C2DT31409F
Citation: Dalton Trans., 2012,41, 14197-14203
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    Selective synthesis of 6,8-di-t-butylated flavan over Zn–Al containing mesoporous silica catalysts

    M. Selvaraj, P. K. Sinha, D.-W. Park, I. Kim, S. Kawi and C. S. Ha, Dalton Trans., 2012, 41, 14197
    DOI: 10.1039/C2DT31409F

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