Synthesis 2015; 47(15): 2185-2187
DOI: 10.1055/s-0034-1380432
psp
© Georg Thieme Verlag Stuttgart · New York

A Practical and Cost-Effective Method for the Synthesis of Bicyclo[2.2.2]octane-1,4-dicarboxylic Acid

Nicolas Le Marquer
Institut des Molécules et Matériaux du Mans, IMMM, UMR CNRS 6283, Université du Maine, 72085 Le Mans, France   Email: [email protected]
,
Mathieu Yves Laurent
Institut des Molécules et Matériaux du Mans, IMMM, UMR CNRS 6283, Université du Maine, 72085 Le Mans, France   Email: [email protected]
,
Arnaud Martel*
Institut des Molécules et Matériaux du Mans, IMMM, UMR CNRS 6283, Université du Maine, 72085 Le Mans, France   Email: [email protected]
› Author Affiliations
Further Information

Publication History

Received: 17 March 2015

Accepted after revision 06 May 2015

Publication Date:
02 July 2015 (online)


Abstract

A short and efficient synthesis of bicyclo[2.2.2]octane-1,4-dicarboxylic acid involving the formation of a semicarbazone is developed, and a reproducible protocol for the reduction of this semicarbazone is described. The use of microwaves significantly shortens the duration of the sequence to the diacid compared to the previously described synthetic method. In addition, by shifting from the use of large amounts of Raney nickel to a solid-phase process, both the safety and cost are improved notably.

Supporting Information

 
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