Skip to main content

Research Repository

Advanced Search

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.

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


Authors

James S. Sharley

Guido Gambacorta

Ana María Collado Pérez

Estela Espinos Ferri

Amadeo Fernandez Miranda

Isabelle Fernández Fernández

Jorge Sanchez Quesada



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.

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

Files





You might also like



Downloadable Citations