Issue 46, 2012

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

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

Supplementary files

Article information

Article type
Paper
Submitted
29 Jun 2012
Accepted
28 Aug 2012
First published
09 Oct 2012

Dalton Trans., 2012,41, 14197-14203

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements