SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2013 , Vol. 33 >Issue 05: 1022 - 1025

DOI: https://doi.org/10.6023/cjoc201211014

Articles

Green Synthesis of α-Benzoin Oxime, and the Selective Control and Separation of Its Cis-Trans Isomers

  • Li Jing ,
  • Xu Shengming ,
  • Li Linyan ,
  • Wang Junlian
Expand
  • Institute of Nuclear and New Energy Technology, Tsinghua University, Beijing 100084

Received date: 2012-11-07

  Revised date: 2012-01-13

  Online published: 2012-01-21

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 51074096, 50734005), and the National Basic Research Program of China (No. 2012CBA01201).

Fold

Abstract

A synthesis and isolation method for α-benzoin oxime was reported. With benzaldehyde as starting material and dicationic imidazolium salt as catalyst, α-benzoin as an important intermediate was synthesized through the mechanism of nitrogen heterocyclic carbine. This method is characterized by mild conditions, low cost, environment friendly and good yield. In the α-benzoin oximation reaction, adjusting the reaction temperature can get selective control of oxime structure for cis-trans isomers which were completely separated by column chromatography using gradient elution.

Key words： α-benzoin oxime; synthesis; cis-trans isomer; separation

Cite this article

Li Jing , Xu Shengming , Li Linyan , Wang Junlian . Green Synthesis of α-Benzoin Oxime, and the Selective Control and Separation of Its Cis-Trans Isomers[J]. Chinese Journal of Organic Chemistry, 2013 , 33(05) : 1022 -1025 . DOI: 10.6023/cjoc201211014

References

[1] Swanson, R. R. US 3224873, 1965 [Chem. Abstr. 1965, 62, p8736b].
[2] Swanson, R. R. US 3284501, 1966 [Chem. Abstr. 1966, 64, p6178f].
[3] Xu, K.; Liang, J. Hydrometall. China 2011, 30, 87 (in Chinese).
(许凯, 粱杰, 湿法冶金, 2011, 30, 87.)
[4] Chen, D. H.; Jiang, Y. Z. CN 1079733, 1993 [Chem. Abstr. 1994, 121, 133694].
[5] Donoho?, T. J.; Jahanshahi, A.; Tucker, M. J.; Bhatti, F. L.; Roslan, I. A.; Kabeshov, M.; Wrigley, G. Chem. Commun. 2011, 47, 5849.
[6] Coldham, I.; Adams, H.; Ashweek, N. J.; Barker, T. A.; Reeder, A. T.; Skilbeck, M. C. Tetrahedron Lett. 2010, 51, 2457.
[7] Safari, J.; Arani, N. M.; Isfahani, A. R. Asian J. Chem. 2011, 23, 495.
[8] Aliyu, H. N.; Ibrahim, B. M. Inter. J. Chem. 2010, 20, 175.
[9] You, L.; Cho, E. J.; Leavitt, J.; Ma, L. C.; Montelione, G. T.; Anslyn, E. V.; Krug, R. M.; Ellington, A.; Robertusa, J. D. Bioorg. Med. Chem. Lett. 2011, 21, 3007.
[10] Joo, C.; Kang, S.; Kim, S. M.; Han, H.; Yang, J. W. Tetrahedron Lett. 2010, 51, 6006.
[11] Chen, C. T.; Kao, J. Q.; Salunke, S. B.; Lin, Y. H. Org. Lett. 2011, 13, 26.
[12] Snow, A. D.; Hu, Q.; Cam, J. A. US 7714170, 2010 [Chem. Abstr. 2010, 152, 547900].
[13] Epple, R.; Cow, C.; Xie, Y.; Azimioara, M.; Russo, R.; Wang, X.; Wityak, J.; Karanewsky, D. S.; Tuntland, T.; Nguyêñ-Tran, V. T.; Cuc, N. C.; Huang, D.; Saez, E.; Spalding, T.; Gerken, A.; Iskandar, M.; Seidel, H. M.; Tian, S. S. J. Med. Chem. 2010, 53, 77.
[14] Marion, N.; Diez-Gonzalez, S.; Nolan, S. P. Angew. Chem., Int. Ed. 2007, 46, 2988.
[15] Biju, A. T.; Kuhl, N.; Glorius, F. Acc. Chem. Res. 2011, 44, 1182.
[16] Xu, L. W.; Gao, Y.; Yin, J.; Li, L.; Xia, C. Tetrahedron Lett. 2005, 46, 5317.
[17] Storey, J. M. D.; Williamson, C. Tetrahedron Lett. 2005, 46, 7337.
[18] Enders, D.; Han, J. Tetrahedron: Asymmetry 2008, 19, 1367.
[19] Chiarotto, I.; Feroci, M.; Orsini, M.; Feeney, M. M. M.; Inesi, A. Adv. Synth. Catal. 2010, 352, 3287.
[20] Murat, E. M.; Cigdem, Y.; Feray, A. Tetrahedron Lett. 2010, 51, 4509.
[21] Aupoix, A.; Pégot, B.; Thanh, G. V. Tetrahedron 2010, 66, 1352.
[22] Tong, Z. T.; Gan, G. Z. Acta Chim. Sinica 1983, 41, 380 (in Chinese).
(童曾寿, 甘贵之, 化学学报, 1983, 41, 380.)
[23] Li, Z. F.; Luo, F. Y. Chin. J. Appl. Chem. 2001, 18, 473 (in Chinese).
(李再峰, 罗富英, 应用化学, 2001, 18, 473.)
[24] Cao, Y. Liaoning Chem. Ind. 2008, 37, 796 (in Chinese).
(曹禹, 辽宁化工, 2008, 37, 796.) Li, W. H.;
[25] Li, H.; Zou, X. N. Hebei Chem. Ind. 2010, 33(11), 31 (in Chinese).
(李伟宏, 李鸿, 邹向南, 河北化工, 2010, 33(11), 31.)
Options
Outlines

/

〈 〉