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

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 fro...

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Bibliographic Details
Published in:Molecules
Main Authors: Ramon Canela, Mercè Torres, Jordi Eras, Núria Sala, Mireia Oromí-Farrús
Format: Article in Journal/Newspaper
Language:English
Published: MDPI AG 2009
Subjects:
(S)-1-bromomethyl-1-heptanol
(S)-1-chloromethyl-1-heptanol
lipases
enzymatic resolution
Organic chemistry
QD241-441
Antarc*
Antarctica
Online Access:https://doi.org/10.3390/molecules14104275
https://doaj.org/article/7d741ef3b3914fe08b9faa9ea09cd395
Description
Summary: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].

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