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Synthesis of δ-Decalactone
Corresponding Author(s) : Guangxue Li
Asian Journal of Chemistry,
Vol. 25 No. 8 (2013): Vol 25 Issue 8
Abstract
The application and shortcomings of typical synthetic method of title d-decalactone was introduced in brief. A synthesis of 2-pentylidene cyclopentanone starting from cyclopentanone and n-valeraldehyde through aldol condensation, followed by dehydration, was studied and the yield reached 86.3 %. Then 2-pentenyl cyclopentanone was prepared in a yield of 91.5 % from 2-pentylidene cyclopentanone with a hydrogenation methodology under atmospheric pressure and use Pt/C as catalytic. Through Baeyer-Villiger oxidation, d-decalactone was synthesized in a yield of 61.2 %. Experiments by orthogonal experiment method to optimize the reaction conditions to determine the response of a reasonable process parameters and the analysis of the factors affecting the reactions. The structures and compositions of these compounds were accomplished by IR and GC-MS.
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References
G.X. Wu and D.H. Hu, Flavour Fragrance Cosmetics, p. 21 (2000).
C.Y. Fan, Spices and Its application, Beijing: Chemical Industry Press, p. 19 (1990).
A. Corma, S. Iborra, M. Mifsud, M. Renz and M. Susarte, Adv. Synth. Catal. 346, 257 (2004).
P. Manat and J. Prapanpong, Tetrahedron Lett., 26, 2253 (1985).
G.X. Wu, D.H. Hu, C.H. Yang and Q.H. Kuang, Fine Specialty Chem., 17 (2001).
G. Bernd, H. Thomas and L.N. Ulrich, Chem. Ber., 117, 859 (1984).
Y.W. Zhao, W.M. Jia, Z.J. Wang and L.D. Liang, J. Shanghai Inst. Technol. (Nat. Sci.), 11, 100 (2011).
G.F. Ma, The New Baeyer-Villiger Catalytic Oxidation Reaction, Northwest Normal University (2007).
J.W. Liu, Nanjing Univ. Sci. Technol., (2006).
J.F. Xu, Y. Shen and J.J. Jiang, Fine Specialty Chem., 12, 12 (2004).
L.Z. Gao, Z.L. Cai and B.F. Wang, J. Luo Yang Univ., 15, 45 (2000).
J.W. Liu, T.T. Yan, H. Xuan, W. Mao and X.H. Peng, Jiangsu Chem. Ind., 33, 146 (2005).