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Synthesis and Crystal Structure of 2-(4-Chlorophenyl)-5-Ethyl-1,3-Dioxane-5-Carboxylic Acid
Corresponding Author(s) : Xian-You Yuan
Asian Journal of Chemistry,
Vol. 26 No. 19 (2014): Vol 26 Issue 19
Abstract
A new synthetic intermediate 2-(4-chlorophenyl)-5-ethyl-1,3-dioxane-5-carboxylic acid, derived from the reaction of 2,2'-bis(hydroxymethyl)butyric acid with 4-chlorobenzaldehyde, has been prepared and characterized by IR spectra and 1H NMR spectroscopy. The definitive molecular structure was determined by single-crystal X-ray analyses, which revealed that the title compound belongs to monoclinic system with space group P2(1)/n with a = 12.655(3) Å, b = 8.260(2) Å, c = 24.380(6) Å, b = 92.533(2)º, Mr = 270.70, V = 2545.89(11) Å3, Dc = 1.412 g/cm3, Z = 8, μ = 0.304 mm-1, F(000) = 1136, R = 0.0336, wR = 0.0815. In the title compound, there are two independent molecules in the asymmetric unit. The 1,3-dioxane ring adopts a chair conformation and the 4-chlorophenyl substituent occupies an equatorial site. In the crystal, adjacent molecules are connected by O-H...O hydrogen bonding interactions into a dimer.
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- M.H. He and Q.J. Liao, Chin. J. Med. Chem., 14, 350 (2004).
- Z.F. Xie and Y.J. Feng, J. Surfact. Deterg., 13, 51 (2010); doi:10.1007/s11743-009-1152-4.
- Y. Itoh, J. Horiuchi and K. Takahashi, Colloids Surf. A, 308, 118 (2007); doi:10.1016/j.colsurfa.2007.05.037.
- N. Alemdar, A.T. Erciyes and N. Bicak, Polymer, 51, 5044 (2010); doi:10.1016/j.polymer.2010.08.066.
- G.W. Wang, X.Y. Yuan, Y.C. Liu, X.-G. Lei and Q.-X. Guo, J. Am. Oil Chem. Soc., 72, 83 (1995); doi:10.1007/BF02635783.
- X.Y. Yuan, N.F. Yang, H.A. Luo and Y.J. Liu, Chin. J. Org. Chem., 25, 1049 (2005).
- G.W. Wang, Y.C. Liu, X.Y. Yuan, X.G. Lei and Q.-X. Guo, J. Colloid Interface Sci., 173, 49 (1995); doi:10.1006/jcis.1995.1295.
- G.W. Wang, X.Y. Yuan, Y.C. Liu, Q.X. Guo and X.G. Lei, Indian J. Chem., 35B, 583 (1996).
- G.W. Wang, X.Y. Yuan, Y.C. Liu and X.G. Lei, J. Am. Oil Chem. Soc., 71, 727 (1994); doi:10.1007/BF02541429.
- G.M. Sheldrick, SHELX-97. Program Package for Crystal Structure Solution and Refinement; University of Gottingen: Germany (1997).
- M. Laing, P. Sommerville, S.E. Drewes and M.W. Drewes, S. Afr. J. Chem., 37, 27 (1984).
- X.Q. Sun, S.L. Yu, Z.Y. Li and Y. Yang, J. Mol. Struct., 973, 152 (2010); doi:10.1016/j.molstruc.2010.03.062.
- X.Y. Wang, J.H. Shi, M. Zhang and S.W. Ng, Acta Crystallogr. Sect. E Struct. Rep. Online, 66, o426 (2010); doi:10.1107/S1600536810002400.
References
M.H. He and Q.J. Liao, Chin. J. Med. Chem., 14, 350 (2004).
Z.F. Xie and Y.J. Feng, J. Surfact. Deterg., 13, 51 (2010); doi:10.1007/s11743-009-1152-4.
Y. Itoh, J. Horiuchi and K. Takahashi, Colloids Surf. A, 308, 118 (2007); doi:10.1016/j.colsurfa.2007.05.037.
N. Alemdar, A.T. Erciyes and N. Bicak, Polymer, 51, 5044 (2010); doi:10.1016/j.polymer.2010.08.066.
G.W. Wang, X.Y. Yuan, Y.C. Liu, X.-G. Lei and Q.-X. Guo, J. Am. Oil Chem. Soc., 72, 83 (1995); doi:10.1007/BF02635783.
X.Y. Yuan, N.F. Yang, H.A. Luo and Y.J. Liu, Chin. J. Org. Chem., 25, 1049 (2005).
G.W. Wang, Y.C. Liu, X.Y. Yuan, X.G. Lei and Q.-X. Guo, J. Colloid Interface Sci., 173, 49 (1995); doi:10.1006/jcis.1995.1295.
G.W. Wang, X.Y. Yuan, Y.C. Liu, Q.X. Guo and X.G. Lei, Indian J. Chem., 35B, 583 (1996).
G.W. Wang, X.Y. Yuan, Y.C. Liu and X.G. Lei, J. Am. Oil Chem. Soc., 71, 727 (1994); doi:10.1007/BF02541429.
G.M. Sheldrick, SHELX-97. Program Package for Crystal Structure Solution and Refinement; University of Gottingen: Germany (1997).
M. Laing, P. Sommerville, S.E. Drewes and M.W. Drewes, S. Afr. J. Chem., 37, 27 (1984).
X.Q. Sun, S.L. Yu, Z.Y. Li and Y. Yang, J. Mol. Struct., 973, 152 (2010); doi:10.1016/j.molstruc.2010.03.062.
X.Y. Wang, J.H. Shi, M. Zhang and S.W. Ng, Acta Crystallogr. Sect. E Struct. Rep. Online, 66, o426 (2010); doi:10.1107/S1600536810002400.