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

Cyclamen aldehyde synthesis: aldol condensation followed by hydrogenation over ruthenium catalyst 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. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Research on Chemical Intermediates Springer Journals

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

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Publisher
Springer Netherlands
Copyright
Copyright © 2015 by Springer Science+Business Media Dordrecht
Subject
Chemistry; Catalysis; Physical Chemistry; Inorganic Chemistry
ISSN
0922-6168
eISSN
1568-5675
D.O.I.
10.1007/s11164-015-1948-y
Publisher site
See Article on Publisher Site

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.

Journal

Research on Chemical IntermediatesSpringer Journals

Published: Feb 15, 2015

References

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