The compound, 2-hydroxy-[1,2-di(pyridin-2-yl)]ethane-1-one, 1, was isolated from the reaction of 2-pyridinecarboxaldehyde and 2-pyridinemethanol at 140°C without catalyst or solvent and characterized by1H-NMR and IR spectral data. The compound 1 was treated with ethyl acetate to produce the 1,2-di(pyridin-2-yl)ethane-1,2-dione, 2. When 2 was dissolved in an excess of CH3OH, crystals of 1,2-dimethoxy-1,2-di(pyridin-2-yl)-1,2-ethanediol, 3, were obtained. The molecular and crystal structure of 3 was determined by single crystal X-ray diffraction. The compound crystallizes in the monoclinic system belonging to the P21/n space group with a = 6.867(2) Å, b=9.546(4) Å, c=10.522(5) Å, α=90°, β=98.48(4)°, γ=90°. The asymmetric unit comprises two molecules of 3. Although the di-hemiketal was obtained in crystal form, it was found to be unstable, because its IR spectrum changed after a short time, indicating that it had been converted back to the original diketone, 2. The IR showed signals at 1713, and 1690 due to νC =O assigned to di-ketone group.
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Crystallographic data (excluding structure factors) reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 253718. Copies of available material can be obtained, free of charge, on application to the CCDC, 12 Union Road, Cambridge CB2 IEZ, UK (fax: +44-(0)1223-336033 or e-mail: deposit@ccdc.cam.ac.uk).
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Percino, M.J., Chapela, V.M., Romero, S. et al. Synthesis of 1,2-dimethoxy-1,2-di(pyridin-2-yl)-1,2-ethanediol: Crystal and molecular structure determination. J Chem Crystallogr 36, 303–308 (2006). https://doi.org/10.1007/s10870-005-9064-2
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DOI: https://doi.org/10.1007/s10870-005-9064-2