Issue 4, 2005

Synthesis of 3-(4-tert-butylphenyl)-2-propen-1-one, a precursor to Lilial®, via an aldol condensation in an ionic liquid

Abstract

An efficient synthesis of a precursor to Lilial®, based on an aldol condensation in an ionic liquid, is described, utilising piperidine as the base catalyst. The yields obtained with this methodology are significantly increased in comparison with those reported in organic solvents to date. In the ionic liquid, the self-aldol condensation of propanal is suppressed and leads to an increased selectivity with respect to the cross-aldol condensation product without the need to use an excess of 4-tert-butylbenzaldehyde to obtain high selectivities.

Graphical abstract: Synthesis of 3-(4-tert-butylphenyl)-2-propen-1-one, a precursor to Lilial®, via an aldol condensation in an ionic liquid

Article information

Article type
Paper
Submitted
19 Oct 2004
Accepted
01 Mar 2005
First published
15 Mar 2005

Green Chem., 2005,7, 224-229

Synthesis of 3-(4-tert-butylphenyl)-2-propen-1-one, a precursor to Lilial®, via an aldol condensation in an ionic liquid

P. N. Davey, S. A. Forsyth, H. Q. N. Gunaratne, C. Hardacre, A. McKeown, S. E. J. McMath, D. W. Rooney and K. R. Seddon, Green Chem., 2005, 7, 224 DOI: 10.1039/B416021E

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