Analytical Sciences

[BMIM][PF₆] Promotes the Synthesis of Halohydrin Esters from Diols Using Potassium Halides

Mireia OROMÍ-FARRÚS,* Jordi ERAS,* Gemma VILLORBINA,* Mercè TORRES,** Veronica LLOPIS-MESTRE,*** Tom WELTON,*** and Ramon CANELA*

*Department of Chemistry, University of Lleida, Av. Alcalde Rovira Roure, 191, Lleida 25198, Spain
**Department of Food Technology, University of Lleida, Av. Alcalde Rovira Roure, 191, Lleida 25198, Spain
***Department of Chemistry, Imperial College of London, South Kensington Campus, London SW7 2AZ, United Kingdom

Haloesterification of diverse diols with various carboxylic acids was achieved using potassium halides (KX) as the only halide source in ionic liquids. The best yield was obtained in [BMIM][PF₆] when 1,2-octanediol, palmitic acid and KBr were used. This yield was 85% and the regioisomer with the bromine in primary position was present in a 75:25 ratio. The regioisomeric ratio could be improved using either KCl or some phenylcarboxylic acids. [BMIM][PF₆] acts as both reaction media and catalyst of the reaction. To the best of our knowledge, this type of combined reaction using an ionic liquid is unprecedented. The other solvents tested did not lead either to the same yield or to the same regioisomeric ratio.

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