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Synthesis and Crystal Structure of (5-Ethyl-2-methyl-2-phenyl-1,3-dioxan-5-yl)methanol
Corresponding Author(s) : Xian-You Yuan
Asian Journal of Chemistry,
Vol. 27 No. 6 (2015): Vol 27 Issue 6
Abstract
A new compound (5-ethyl-2-methyl-2-phenyl-1,3-dioxan-5-yl)methanol, obtained from the reaction of 2,2-bis(hydroxymethyl)butanol with acetophenone, has been synthesized and characterized by IR and 1H NMR. Single crystal X-ray diffraction analyses indicated that the title compound belongs to tetragonal system with space group I4(1)/a with a = 29.921(2) Å, b = 29.921(2) Å, c = 5.9627(9) Å. Mr = 236.30, V = 5338.1(10) Å3, Dc = 1.176 g/cm3, Z = 16, μ = 0.081 mm-1, F(000) = 2048, R = 0.0595, wR = 0.1645. In the title compound, the 1,3-dioxane ring adopts a chair conformation and the phenyl substituent occupies an equatorial site. In the crystal, adjacent four molecules are connected by O-H···O hydrogen bonding interactions into a tetramer.
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- L. Yuan, G.C. Ou, J.H. Shi, M. Zhang and X. Yuan, Chin. J. Org. Chem., 33, 1817 (2013); doi:10.6023/cjoc201303003.
- Z.F. Xie and Y.J. Feng, J. Surfact. Deterg., 13, 51 (2010); doi:10.1007/s11743-009-1152-4.
- M. Zhang, G.K. Jia, L. Yuan and X.Y. Yuan, Z. Kristallogr. NCS, 228, 393 (2013); doi:10.1524/ncrs.2013.0197.
- M.Y. Ye and G. Zhou, Sci. China Ser. Biol. Chem., 43, 551 (2013).
- H.T.T. Duong, F. Hughes, S. Sagnella, M. Kavallaris, A. Macmillan, R. Whan, J. Hook, T.P. Davis and C. Boyer, J. Mol. Pharm., 9, 3046 (2012); doi:10.1021/mp300144y.
- F. Rosas, J. Lezama, J.R. Mora, A. Maldonado, T. Cordova and G. Chuchani, J. Phys. Chem. A, 116, 9228 (2012); doi:10.1021/jp305179n.
- G.W. Wang, X.Y. Yuan, Y.C. Liu, Q.X. Guo and X.G. Lei, Indian J. Chem., 35B, 583 (1996).
- J. Miao, H. Wan, Y. Shao, G. Guan and B. Xu, J. Mol. Catal. Chem., 348, 77 (2011); doi:10.1016/j.molcata.2011.08.005.
- J. Akbari, A. Heydari, H. Reza Kalhor and S.A. Kohan, J. Comb. Chem., 12, 137 (2010); doi:10.1021/cc9001313.
- G.M. Sheldrick, SHELX-97. Program Package for Crystal Structure Solution and Refinement; University of Gottingen: Germany (1997).
- D.A. Evans, D.L. Rieger and J.R. Gage, Tetrahedron Lett., 31, 7099 (1990); doi:10.1016/S0040-4039(00)97250-2.
- S.D. Rychnovsky, B. Rogers and G. Yang, J. Org. Chem., 58, 3511 (1993); doi:10.1021/jo00065a011.
- S.D. Rychnovsky, B.N. Rogers and T.I. Richardson, Acc. Chem. Res., 31, 9 (1998); doi:10.1021/ar960223n.
References
L. Yuan, G.C. Ou, J.H. Shi, M. Zhang and X. Yuan, Chin. J. Org. Chem., 33, 1817 (2013); doi:10.6023/cjoc201303003.
Z.F. Xie and Y.J. Feng, J. Surfact. Deterg., 13, 51 (2010); doi:10.1007/s11743-009-1152-4.
M. Zhang, G.K. Jia, L. Yuan and X.Y. Yuan, Z. Kristallogr. NCS, 228, 393 (2013); doi:10.1524/ncrs.2013.0197.
M.Y. Ye and G. Zhou, Sci. China Ser. Biol. Chem., 43, 551 (2013).
H.T.T. Duong, F. Hughes, S. Sagnella, M. Kavallaris, A. Macmillan, R. Whan, J. Hook, T.P. Davis and C. Boyer, J. Mol. Pharm., 9, 3046 (2012); doi:10.1021/mp300144y.
F. Rosas, J. Lezama, J.R. Mora, A. Maldonado, T. Cordova and G. Chuchani, J. Phys. Chem. A, 116, 9228 (2012); doi:10.1021/jp305179n.
G.W. Wang, X.Y. Yuan, Y.C. Liu, Q.X. Guo and X.G. Lei, Indian J. Chem., 35B, 583 (1996).
J. Miao, H. Wan, Y. Shao, G. Guan and B. Xu, J. Mol. Catal. Chem., 348, 77 (2011); doi:10.1016/j.molcata.2011.08.005.
J. Akbari, A. Heydari, H. Reza Kalhor and S.A. Kohan, J. Comb. Chem., 12, 137 (2010); doi:10.1021/cc9001313.
G.M. Sheldrick, SHELX-97. Program Package for Crystal Structure Solution and Refinement; University of Gottingen: Germany (1997).
D.A. Evans, D.L. Rieger and J.R. Gage, Tetrahedron Lett., 31, 7099 (1990); doi:10.1016/S0040-4039(00)97250-2.
S.D. Rychnovsky, B. Rogers and G. Yang, J. Org. Chem., 58, 3511 (1993); doi:10.1021/jo00065a011.
S.D. Rychnovsky, B.N. Rogers and T.I. Richardson, Acc. Chem. Res., 31, 9 (1998); doi:10.1021/ar960223n.