International Flavors & Fragrances Inc.

James S Sharley

Ian R Baxendale

Ana Maria Collado Perez

Estela Espinos Ferri

Amadeo Fernández Miranda

Isabelle Fernandez Fernandez

Ana Maria Collado Pérez

Jorge Sánchez Quesada

Ana Maria Collado PÉREZ

Disclosed is a chemical process of preparing dehydrohedione from Hedione via &#x3b1;-chlorination and elimination steps. The process can be conducted in a one-pot process or in a continuous reactor system. Accordingly, a simple and cost effective process of preparing cis-Hedione enriched products is developed through reduction of dehydrohedione in the presence of a chiral catalyst system.

Chemical process of preparing dehydrohedione

Amine-catalyzed formation of cyclic allylic nitro compounds via nitro-aldol reaction is disclosed. A greener solvent and a cheaper, more robust catalyst than in previous reports are used in the nitro-aldol reaction. After screening a range of catalysts the reaction is developed as a selective method of synthesis of &#x3b1;-dehydroherbac and the scope is demonstrated with a small collection of additional substrates.

Preparation of cyclic allylic nitro compounds

Copper(II) bromide mediated oxidation of acylated enol and use of the reaction in the synthesis of &#x3b1;,&#x3b2;-unsaturated or &#x3b1;-bromo ketones or aldehydes are disclosed. The method provides an efficient and practical process for manufacturing dehydrohedione (DHH) and many other versatile &#x3b1;,&#x3b2;-unsaturated or &#x3b1;-bromo ketones or aldehydes in large scales to avoid using precious metal compounds.

Methods of preparing &#x3b1;,&#x3b2;-unsaturated or &#x3b1;-halo ketones and aldehydes

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Biggleswade, United Kingdom

James S Sharley