A simple one-pot oxidation protocol for the synthesis of dehydrohedione from Hedione. (5th November 2022)

• Record Type: Journal Article
• Authors: Sharley, James S.; Gambacorta, Guido; Collado Pérez, Ana María; Ferri, Estela Espinos; Miranda, Amadeo Fernandez; Fernández, Isabelle Fernández; Quesada, Jorge Sanchez; Baxendale, Ian R.
• Is Part Of: Tetrahedron. Volume 126(2022)
• Publication Date: 2022-11-05
• Subjects: Hedione -- Fragrance -- Chlorination -- Dehydrochlorination -- Trichloroisocyanuric acid -- Sulfuryl chloride -- Process development -- Dehydrohedione -- Oxidation -- Flow chemistry; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2022.133068
• Languages: English
• ISSNs: 0040-4020

Abstract

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. Graphical abstract: Image 1