Synthesis and Crystal Structure of (2,5-Dimethyl-2-phenyl-1,3-dioxane-5-yl) methanoic Acid

Guo-Kai Jia; Lin Yuan; Min Zhang; Gauang-Chuan Ou; Xian-You Yuan

doi:10.14233/ajchem.2015.18224

Issue

Vol. 27 No. 8 (2015): Vol 27 Issue 8

Issue Published : April 27, 2015

This work is licensed under a Creative Commons Attribution 4.0 International License.

Synthesis and Crystal Structure of (2,5-Dimethyl-2-phenyl-1,3-dioxane-5-yl) methanoic Acid

https://doi.org/10.14233/ajchem.2015.18224

Guo-Kai Jia

Department of Biology and Chemistry, Hunan University of Science and Engineering, Yongzhou, Hunan Province, P.R. China

Lin Yuan

Department of Biology and Chemistry, Hunan University of Science and Engineering, Yongzhou, Hunan Province, P.R. China; Key Laboratory of Functional Organometallic Materials of Hunan Province College, Hengyang Normal University, Hengyang, Hunan Province, P.R. China

Min Zhang

Department of Biology and Chemistry, Hunan University of Science and Engineering, Yongzhou, Hunan Province, P.R. China

Gauang-Chuan Ou

Xian-You Yuan

Department of Biology and Chemistry, Hunan University of Science and Engineering, Yongzhou, Hunan Province, P.R. China

Corresponding Author(s) : Xian-You Yuan

yuanxianzhangmin@163.com

Asian Journal of Chemistry, Vol. 27 No. 8 (2015): Vol 27 Issue 8
Article Published : April 27, 2015

Abstract

A new cyclic compound (2,5-dimethyl-2-phenyl-1,3-dioxane-5-yl) methanoic acid was prepared from the reaction of acetophenone with 2,2-bis(hydroxymethyl) propionic acid and characterized by ¹H NMR and FT-IR. The molecular structure was presented by single crystal X-ray diffraction analyses, which shows that the title compound belongs to orthorhombic system with space group Cmca with a = 10.011(3) Å, b = 6.421(3) Å, c = 37.688(11) Å. Mr = 236.26, V = 2422.6(13) Å³, Dc = 1.296 g/cm³, Z = 8, μ = 0.096 mm^-1, F(000) = 1008, R = 0.0553, wR = 0.1699. In the title compound, the 1,3-dioxane ring adopts a chair conformation and the phenyl substituent occupies an axial site. In the crystal, adjacent two molecules are connected by O-H...O hydrogen bonding to form a dimer.

Keywords

1 3-Dioxane 2 2-bis(Hydroxymethyl) propionic acid

Jia, G.-K., Yuan, L., Zhang, M., Ou, G.-C., & Yuan, X.-Y. (2015). Synthesis and Crystal Structure of (2,5-Dimethyl-2-phenyl-1,3-dioxane-5-yl) methanoic Acid. Asian Journal of Chemistry, 27(8), 2833–2835. https://doi.org/10.14233/ajchem.2015.18224

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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.

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.

G.W. Wang, Y.C. Liu, X.Y. Yuan, X.G. Lei and Q.X. Guo, J. Colloid Interf. 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. Zhang, G.K. Jia, L. Yuan and X.Y. Yuan, Z. Kristallogr. NCS, 228, 393 (2013); doi:10.1524/ncrs.2013.0197.

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., E66, o426 (2010); doi:10.1107/S1600536810002400.

G.K. Jia, L. Yuan, M. Zhang and X.Y. Yuan, Acta Crystallogr., E68, o2037 (2012); doi:10.1107/S1600536812025019.

S.D. Rychnovsky, B. Rogers and G. Yang, J. Org. Chem., 58, 3511 (1993); doi:10.1021/jo00065a011.

Issue

Vol. 27 No. 8 (2015): Vol 27 Issue 8

Synthesis and Crystal Structure of (2,5-Dimethyl-2-phenyl-1,3-dioxane-5-yl) methanoic Acid

Corresponding Author(s) : Xian-You Yuan

Abstract

Keywords

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