Resolution of racemic trans-1,2-cyclohexanediol with tartaric acid

Péter Molnár, Paul Thorey, György Bánsághi, Edit Székely, L. Poppe, Anna Tomin, S. Kemény, E. Fogassy, B. Simándi

Research output: Contribution to journalArticle

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Abstract

A simple method for the resolution of racemic trans-1,2-cyclohexanediol enantiomers is presented in this paper. The chiral discrimination was performed by tartaric acid via diastereomeric complex formation. The diastereomeric complexes were formed by adding the resolving agent to the racemic diol in a 0.5:1 molar ratio. The (2R,3R)-(+)-tartaric acid forms stable diastereomeric complex with (1R,2R)-(-)-cyclohexanediol. Supercritical carbon dioxide extraction was applied to the separation of the mixture of diastereomeric complexes and uncomplexed diol enantiomers. We found unexpected optimal conditions according to the 32 factorial design on the resolution efficiency within the studied range of the extraction pressure and temperature. In the best cases, the (1S,2S)- and (1R,2R)-diol enantiomers were obtained with ee(1S,2S) = 62% and ee(1R,2R) = 93% enantiomeric excess in one equilibrium stage, respectively.

Original languageEnglish
Pages (from-to)1587-1592
Number of pages6
JournalTetrahedron Asymmetry
Volume19
Issue number13
DOIs
Publication statusPublished - Jul 11 2008

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Enantiomers
enantiomers
acids
Acids
Complex Mixtures
Carbon Dioxide
factorial design
Pressure
Temperature
discrimination
carbon dioxide
Carbon dioxide
tartaric acid
1,2-cyclohexanediol
temperature

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry
  • Materials Chemistry
  • Drug Discovery

Cite this

Resolution of racemic trans-1,2-cyclohexanediol with tartaric acid. / Molnár, Péter; Thorey, Paul; Bánsághi, György; Székely, Edit; Poppe, L.; Tomin, Anna; Kemény, S.; Fogassy, E.; Simándi, B.

In: Tetrahedron Asymmetry, Vol. 19, No. 13, 11.07.2008, p. 1587-1592.

Research output: Contribution to journalArticle

Molnár P, Thorey P, Bánsághi G, Székely E, Poppe L, Tomin A et al. Resolution of racemic trans-1,2-cyclohexanediol with tartaric acid. Tetrahedron Asymmetry. 2008 Jul 11;19(13):1587-1592. https://doi.org/10.1016/j.tetasy.2008.06.023
Molnár, Péter ; Thorey, Paul ; Bánsághi, György ; Székely, Edit ; Poppe, L. ; Tomin, Anna ; Kemény, S. ; Fogassy, E. ; Simándi, B. / Resolution of racemic trans-1,2-cyclohexanediol with tartaric acid. In: Tetrahedron Asymmetry. 2008 ; Vol. 19, No. 13. pp. 1587-1592.
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