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

• Published in: Molecules
• Main Authors: Mireia Oromí-Farrús, Jordi Eras, Núria Sala, Mercè Torres, Ramon Canela
• Format: Text
• Language: English
• Published: Molecular Diversity Preservation International 2009
• Subjects: ( S )-1-bromomethyl-1-heptanol; ( S )-1-chloromethyl-1-heptanol; lipases; enzymatic resolution; Antarc*; Antarctica
• Online Access: https://doi.org/10.3390/molecules14104275

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].