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Enol tautomer of the acetate ester of 3-methoxy-4-hydroxyphenylpyruvic acid: Crystallographic and NMR spectroscopic evidence

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Abstract

The para acetate ester azlactone of vanillin 2 was synthesized from vanillin 1 and hydrolyzed with sodium hydroxide. The yielded product 3 was investigated with X-ray Crystallographic and nuclear magnetic resonance techniques. Compound 3 crystallized in the orthorhombic Pbca space group (Z = 8) and with cell dimensions a = 14.732(2), b = 12.756(3), c = 12.747(6)Å revealing the enolate tautomer and not the keto form of 3-methoxy-4-hydroxyphenylpyruvic acid as the acetate ester. The structure exhibited the pyruvic acid side chain in the trans extended conformation. A single proton on the benzylic carbon atom further suggested the existence of the enolate tautomer form of 3 in solution. The chemical shift values and peak integration in the NMR spectra add additional support to this finding.

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References

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Authors and Affiliations

  1. Department of Pharmacy, University of the Witwatersrand, 7 York Road, Parktown, 2193, Republic of South Africa

    P. P. Haasbroek

  2. Department of Pharmacology, Potchefstroom University for C. H. E., Potchefstroom, 2520, Republic of South Africa

    D. W. Oliver

  3. ER 61 C.N.R.S., Laboratoire de Chimie Analytique, U.F.R. des Sciences Pharmaceutiques, Université de Bordeaux II, 3 Place de la Victoire, 33076, Bordeaux Cedex, France

    A. J. M. Carpy

Authors
  1. P. P. Haasbroek
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  2. D. W. Oliver
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  3. A. J. M. Carpy
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Haasbroek, P.P., Oliver, D.W. & Carpy, A.J.M. Enol tautomer of the acetate ester of 3-methoxy-4-hydroxyphenylpyruvic acid: Crystallographic and NMR spectroscopic evidence. Journal of Chemical Crystallography 28, 193–196 (1998). https://doi.org/10.1023/A:1022418210170

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  • DOI: https://doi.org/10.1023/A:1022418210170

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