An efficient synthesis of a precursor to Lilial(R), 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.
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Davey, P. N., Forsyth, S., Gunaratne, N., Hardacre, C., McKeown, A., McMath, S. E. J., Rooney, D., & Seddon, K. (2005). Synthesis of 3-(4-tert-butylphenyl)-2-propen-1-one, a precursor to Lilial (R), via an aldol condensation in an ionic liquid. Green Chemistry, 7(4), 224-229. https://doi.org/10.1039/b416021e