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

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

• ^aDepartment of Chemistry, University of Durham, South Road, Durham, DH1 3LE, United Kingdom
• ^bInternational Flavours & Fragrances Inc., Avda Felipe Klein 2, 12580, Benicarló, Castellón, Spain

A new method for the oxidiation 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.

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