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  Home > JCE Print > Journal of Chemical Education > Issues > 2004  > November  >
In the Laboratory
Synthesis and Resolution of the Atropisomeric 1,1'-Bi-2-naphthol: An Experiment in Organic Synthesis and 2-D NMR Spectroscopy
Kendrew K. W. Mak
Department of Chemistry, The Chinese Univeristy of Hong Kong, Shatin, Hong Kong, P. R. China
Cover
November 2004
Vol. 81 No. 11
p. 1636
Abstract
The synthesis and resolution of the atropisomeric 1,1'-bi-2-naphthol illustrates several important concepts in organic chemistry and serves as a good experiment for organic chemistry laboratory course of intermediate to advanced levels. Racemic 1,1'-bi-2-naphthol is synthesized by the oxidative coupling of 2-naphthol and is resolved into the enantiopure form by the selective inclusion compound formation of the R enantiomer with (-)-N-benzylcinchonidinium chloride. The enantiomeric excess of the products are determined by chiral HPLC. The naphthol unit of 1,1'-bi-2-naphthol is composed of a benzene and a phenol fused together. Both 1H and 13C NMR spectra show complicated and overlapping signals in the aromatic region and complete signal assignment is extremely difficult. Unambiguous signal assignment is made possible with the help of various 2-D NMR techniques such as COSY, HMQC, and COLOC. It serves as an advanced exercise for spectroscopic structural identification of organic compounds.
Supplement
Detailed experimental procedures for the students, suggestions for instructors, instrumentation methods, detailed NMR analysis, NMR spectra, and HPLC chromatograms are available.
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*  Citation
 Mak, Kendrew K. W. J. Chem. Educ. 2004 81 1636.
*  Keywords
 Chromatography; Laboratory Instruction; NMR Spectrometry; Organic Chemistry; Organic Synthesis
*  History
 Created:
Last Updated:		 September 27, 2004
October 5, 2004
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