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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,*
Received: 31 August 2009; in revised form: 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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

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.

AMA Style

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(10):4275-4283.

Chicago/Turabian Style

Oromí-Farrús, Mireia; Eras, Jordi; Sala, Núria; Torres, Mercè; Canela, Ramon. 2009. "Preparation of (S)-1-Halo-2-octanols Using Ionic Liquids and Biocatalysts." Molecules 14, no. 10: 4275-4283.


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