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Cyclamen aldehyde synthesis: aldol condensation followed by hydrogenation over ruthenium catalyst

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Abstract

Cyclamen aldehyde is a fragrant substance with the scent of cyclamen or lily-of-the-valley. In this work, the desired cyclamen aldehyde was prepared by two-step synthesis. At the first step, aldol condensation of 4-isopropylbenzaldehyde and propanal was carried out. The influence of used catalyst (potassium hydroxide and sodium methoxide) and propanal amount were tested. Propanal was used in excess and it was added to the reaction mixture dropwise (to prevent its self-condensation to 2-methylpent-2-enal). Resulting mixture of 4-isopropylbenzaldehyde and forcyclamen aldehyde was hydrogenated using different Ru/C catalysts. The products detected in hydrogenation reaction mixture were: desired cyclamen aldehyde, cyclamen alcohol and forcyclamen alcohol. The influence of catalyst type and amount, reaction temperature and hydrogen pressure on the reaction course was tested. The highest yield (19.4 %) was obtained using pressure 10 MPa, temperature 110 °C and 2 wt% of catalyst Ru/C.

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Acknowledgment

Word of thanks to the Ministry of education, youth and sports for financial support from specific university research (MSMT No 20/2014).

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Authors and Affiliations

  1. Department of Organic Technology, Institute of Chemical Technology, Technická 5, Prague, 166 28, Czech Republic

    Eva Vrbková, Tomáš Skýpala, Eliška Vyskočilová & Libor Červený

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  1. Eva Vrbková
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  2. Tomáš Skýpala
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  3. Eliška Vyskočilová
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  4. Libor Červený
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Correspondence to Eva Vrbková.

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Vrbková, E., Skýpala, T., Vyskočilová, E. et al. Cyclamen aldehyde synthesis: aldol condensation followed by hydrogenation over ruthenium catalyst. Res Chem Intermed 41, 9195–9205 (2015). https://doi.org/10.1007/s11164-015-1948-y

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  • DOI: https://doi.org/10.1007/s11164-015-1948-y

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