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

    • James S. Sharleya, Guido Gambacortaa, Ana María Collado Pérezb, Estela Espinos Ferrib, Amadeo Fernandez Mirandab, Isabelle Fernández Fernándezb, Jorge Sanchez Quesadab, Ian R.Baxendalea
    • 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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