Combined Biocatalytic Preparation of (R)-2-Ethylhexanol and 2-Ethylhexyl Laurate

Blaženka Ćiško-Anić, Maja Majerić-Elenkov, Zdenko Hameršak and Vitomir Šunjić*

Ruđer Bošković Institute, Bijenička c. 54, P.O.B.1016, HR-10000 Zagreb, Croatia

Article history:
Received January 25, 1999
Accepted February 15, 1999

Key words:
Pseudomonas sp. lipase, kinetic resolution, (R)-2-ethylhexanol

Summary:
(R)-2-Ethylhexanol (R-1) is prepared in high optical purity (> 99 % enantiomeric excess, e.e.) by the Pseudomonas sp. lipase-catalyzed acylation of racemic 1 using vinyl laurate as the acylating agent that allows the isolation of (R)-1 by distillation. Nonactivated lauric acid proved to be very reactive, affording (R)-1 with > 99 % e.e., but difficulties in down-stream process disfavored its use. 2-Ethylhexyl laurate (3), the other product in this process, is also a commercially valuable material. Recycling of the enzyme and simple isolation of optically pure alcohol (R)-1 makes the method amenable to the scale-up. 

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