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

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

1
,
1
,
2
,
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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Abstract

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 3.0).
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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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