A simple one-pot oxidation protocol for the synthesis of dehydrohedione from Hedione

Sharley, James S.; Gambacorta, Guido; Collado Pérez, Ana María; Ferri, Estela Espinos; Miranda, Amadeo Fernandez; Fernández, Isabelle Fernández; Quesada, Jorge Sanchez; Baxendale, Ian R.

Abstract

A new method for the oxidation of Hedione 1 to dehydrohedione 2, a high value intermediate in the flavour and fragrance industry, has developed based upon one pot α-chlorination-elimination sequence which can be readily scaled. The spontaneous elimination of the α-chloro in methanol was unprecedented and has allowed for the oxidation, typically performed in multiple steps/reactions, to be carried out as a one-pot protocol. A continuous flow process for performing the reaction utilising sulfuryl chloride has also demonstrated allowing for steady, safe evolution of SO2 gas during the reaction.

Citation

Sharley, J. S., Gambacorta, G., Collado Pérez, A. M., Ferri, E. E., Miranda, A. F., Fernández, I. F., Quesada, J. S., & Baxendale, I. R. (2022). A simple one-pot oxidation protocol for the synthesis of dehydrohedione from Hedione. Tetrahedron, 126, https://doi.org/10.1016/j.tet.2022.133068

• Journal Article Type: Article
• Acceptance Date: Sep 30, 2022
• Online Publication Date: Oct 23, 2022
• Publication Date: 2022
• Deposit Date: Dec 21, 2022
• Publicly Available Date: Dec 21, 2022
• Journal: Tetrahedron
• Print ISSN: 0040-4020
• Publisher: Elsevier
• Peer Reviewed: Peer Reviewed
• Volume: 126
• DOI: https://doi.org/10.1016/j.tet.2022.133068
• Public URL: https://durham-repository.worktribe.com/output/1184776