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Molecules 2009, 14(10), 4275-4283; doi:10.3390/molecules14104275

Preparation of (S)-1-Halo-2-octanols Using Ionic Liquids and Biocatalysts

2,*  and 1,*
1 Chemistry Department, Lleida University, 25198-Lleida, Spain 2 Food Technology Department, Lleida University, 25198-Lleida, Spain
* Authors to whom correspondence should be addressed.
Received: 31 August 2009 / Revised: 26 September 2009 / Accepted: 16 October 2009 / Published: 23 October 2009
(This article belongs to the Special Issue Ionic Liquids)
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Preparation of (S)-1-chloro-2-octanol and (S)-1-bromo-2-octanol was carried out by the enzymatic hydrolysis of halohydrin palmitates using biocatalysts. Halohydrin palmitates were prepared by various methods from palmitic acid and 1,2-octanediol. A tandem hydrolysis was carried out using lipases from Candida antarctica (Novozym® 435), Rhizomucor miehei (Lipozyme IM), and “resting cells” from a Rhizopus oryzae strain that was not mycotoxigenic. The influence of the enzyme and the reaction medium on the selective hydrolysis of isomeric mixtures of halohydrin esters is described. Novozym® 435 allowed preparation of (S)-1-chloro-2-octanol and (S)-1-bromo-2-octanol after 1–3 h of reaction at 40 °C in [BMIM][PF6].
Keywords: (S)-1-bromomethyl-1-heptanol; (S)-1-chloromethyl-1-heptanol; lipases; enzymatic resolution (S)-1-bromomethyl-1-heptanol; (S)-1-chloromethyl-1-heptanol; lipases; enzymatic resolution
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Oromí-Farrús, M.; Eras, J.; Sala, N.; Torres, M.; Canela, R. Preparation of (S)-1-Halo-2-octanols Using Ionic Liquids and Biocatalysts. Molecules 2009, 14, 4275-4283.

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