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Title:
PROCESS FOR PREPARING (-)MENTHOL AND SIMILAR COMPOUNDS
Document Type and Number:
WIPO Patent Application WO2002004384
Kind Code:
A3
Abstract:
A process of separating a single desired stereoisomer from a racemic mixture of eight stereoisomers of a compound of formula (III), wherein R1 represents an isopropanol group, an isopropyl group or an isopropylene group, includes the steps of: contacting the racemic mixture in a suitable organic solvent with an esterifying agent and a stereospecific enzyme which stereoselectively esterifies the -OH group of the desired stereoisomer, for a time sufficient to convert a desired percentage of the desired stereoisomer to a compound of formula (IV), wherein R1 is as defined above and R4 is an alkyl or an aryl group, to give a first reaction product including the compound of formula (IV), the organic solvent, the unconverted stereoisomers of the compound of formula (III), excess esterifying agent and by-products of the reaction; and separating the compound of formula (IV) from the first reaction product. The process is of particular application for the production of (-)-menthol.

Inventors:
CHAPLIN JENNIFER ANN (US)
GARDINER NEIL STOCKENSTROM (ZA)
MITRA ROBIN KUMAR (ZA)
PARKINSON CHRISTOPHER JOHN (ZA)
PORTWIG MADRIE (ZA)
BUTANA ANDREW MBONISWA (ZA)
DICKSON MELANIE DARYL EVAN (ZA)
BRADY DEAN (ZA)
MARAIS STEPHANUS FRANCOIS (ZA)
REDDY SHAVANI (ZA)
Application Number:
PCT/IB2001/001008
Publication Date:
June 20, 2002
Filing Date:
June 11, 2001
Export Citation:
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Assignee:
AECI LTD (ZA)
CHAPLIN JENNIFER ANN (US)
GARDINER NEIL STOCKENSTROM (ZA)
MITRA ROBIN KUMAR (ZA)
PARKINSON CHRISTOPHER JOHN (ZA)
PORTWIG MADRIE (ZA)
BUTANA ANDREW MBONISWA (ZA)
DICKSON MELANIE DARYL EVAN (ZA)
BRADY DEAN (ZA)
MARAIS STEPHANUS FRANCOIS (ZA)
REDDY SHAVANI (ZA)
International Classes:
C07B53/00; C07B57/00; C07B61/00; C07C27/02; C07C29/09; C12P41/00; C07C29/19; C07C29/88; C07C35/12; C07C37/16; C07C39/06; (IPC1-7): C07B57/00; C07C35/12; C12P41/00; C07C67/08; C07C29/09
Foreign References:
DE538376C1931-11-14
DE568671C1933-01-24
Other References:
E. CERNIA, ET AL.: "The role of the reaction medium in lipase-catalysed esterifications and transesterifications", CHEMISTRY AND PHYSICS OF LIPIDS, vol. 93, no. 1-2, June 1998 (1998-06-01), Elsevier Science Ireland, Limerick, IE, pages 157 - 168, XP002195581, ISSN: 0009-3084
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