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Issue 10, 2013
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Synthesis of natural fragrance jasminaldehyde using silica-immobilized piperazine as organocatalyst

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Abstract

Jasminaldehyde (α-pentyl cinnamaldehyde) is a natural fragrance that can be produced via aldol-type C–C bond formation between heptanal and benzaldehyde. The use of bases like NaOH to form jasminaldehyde typically leads to significant waste and by-product formation. To provide sustainable options with diminished waste formation and high conversions and selectivities, herein a silica-immobilized piperazine is used as organocatalyst for the jasminaldehyde synthesis either in bio-based solvents (e.g. 2-methyltetrahydrofuran, 2-MeTHF) or in solvent-free conditions (using neat substrates as reaction media). Under reported conditions, a production of ∼7 g jasminaldehyde L−1 h−1 is observed, delivering on-spec conversions and selectivities (>90% each). Selectivity remains unaltered during catalyst recycling, whereas a loss of conversion is significantly observed after reusing the catalyst for several cycles.

Graphical abstract: Synthesis of natural fragrance jasminaldehyde using silica-immobilized piperazine as organocatalyst

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Publication details

The article was received on 06 May 2013, accepted on 09 Jul 2013 and first published on 09 Jul 2013


Article type: Paper
DOI: 10.1039/C3CY00313B
Catal. Sci. Technol., 2013,3, 2732-2736

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    Synthesis of natural fragrance jasminaldehyde using silica-immobilized piperazine as organocatalyst

    M. Pérez-Sánchez and P. D. de María, Catal. Sci. Technol., 2013, 3, 2732
    DOI: 10.1039/C3CY00313B

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