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

doi:10.6023/cjoc201211014

Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (05): 1022-1025.DOI: 10.6023/cjoc201211014 Previous Articles Next Articles

Articles

α-苯偶姻肟的绿色合成及其顺、反异构体的选择性控制与分离

李晶, 徐盛明, 李林艳, 王俊莲

清华大学核能与新能源技术研究院北京 100084

收稿日期:2012-11-07 修回日期:2012-01-13 发布日期:2012-01-21
通讯作者: 徐盛明,smxu@tsinghua.edu.cn;李林艳,lilinyan@tsinghua.edu.cn E-mail:smxu@tsinghua.edu.cn;lilinyan@tsinghua.edu.cn
基金资助:
国家自然科学基金(Nos. 51074096, 50734005)和国家重点基础研究发展计划(No. 2012CBA01201)资助项目.

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

Institute of Nuclear and New Energy Technology, Tsinghua University, Beijing 100084

Received:2012-11-07 Revised:2012-01-13 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).

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]. Chin. J. Org. Chem., 2013, 33(05): 1022-1025.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

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.)

α-苯偶姻肟的绿色合成及其顺、反异构体的选择性控制与分离

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

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Penghui Li, Qingyang Xie, Fuxian Wan, Yuanhong Zhang, Lin Jiang. Synthesis and Fungicidal Activity of Novel Substituted Pyrimidine-5-carboxamides Bearing Cyclopropyl Moiety [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 650-656.
[2]	Fakai Zou, Nengzhong Wang, Hui Yao, Hui Wang, Mingguo Liu, Nianyu Huang. Regio- and Stereo-selective Synthesis of 1β-/3R-Aryl Thiosugar [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 593-604.
[3]	Luyao Li, Zhongwen He, Zhenguo Zhang, Zhenhua Jia, Teck-Peng Loh. Application of Triaryl Carbenium in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 421-437.
[4]	Qinggang Mei, Qinghan Li. Recent Progress of Visible Light-Induced the Synthesis of C(3) (Hetero)arylthio Indole Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 398-408.
[5]	Weiqing Yang, Yanbing Ge, Yuanyuan Chen, Ping Liu, Haiyan Fu, Menglin Ma. Design and Synthesis of Fluorescent 1,8-Napthalimide Derivatives and Their Identification of Cysteine [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 180-194.
[6]	Shihang Yu, Jiawei Liu, Biyu An, Qinghua Bian, Min Wang, Jiangchun Zhong. Asymmetric Synthesis of the Contact Sex Pheromone of Neoclytus acuminatus acuminatus (Fabricius) [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 301-308.
[7]	Qianfan Zhao, Yongzheng Chen, Shiming Zhang. Application and Mechanism Study of Carbon-Based Metal-Free Catalysts in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 137-147.
[8]	Shan Chen, Zhilin Chen, Qiong Hu, Yanshuang Meng, Yue Huang, Pingfang Tao, Liru Lu, Guobao Huang. Recognition of Bis-thiourea Tweezers to Neutral Molecules in Non-Polar Solvent [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 277-281.
[9]	Huakun Wang, Xiaolong Ren, Yining Xuan. Study of the Halide Salt Catalyzed [3＋2] Cycloaddition of α,β-Epoxy Carboxylate with Isocyanate [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 251-258.
[10]	Yukun Jin, Baoyi Ren, Fushun Liang. Visible Light-Mediated Selective C—F Bond Cleavage of Trifluoromethyl Groups and Its Application in Synthesizing gem-Difluoro-Containing Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 85-110.
[11]	Cuiyun Ma, Hailan Luo, Fuhua Zhang, Dan Guo, Shuxing Chen, Fei Wang. Green Biosynthesis, Photophysical Properties and Application of 3-Pyrrolyl BODIPY [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 216-223.
[12]	Bozhen Wang, Jie Zhang, Chunhui Nian, Mingming Jin, Miaomiao Kong, Wulan Li, Wenfei He, Jianzhang Wu. Synthesis and Antitumor Activity of 3,4-Dichlorophenyl Amides [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 232-241.
[13]	Yang Li, Jinding Yuan, Di Zhao. Deep Eutectic Solvent of 1,3-Dimethylurea/L-(+)-Tartaric Acid for the Green Synthesis of (E)-2-Styrylquinoline-3-carboxylic Acid Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3268-3276.
[14]	Dandan Sui, Nannan Cen, Ruoqu Gong, Yang Chen, Wenbo Chen. Supporting-Electrolyte-Free Electrochemical Synthesis of Trifluoromethylated Oxindoles in Continuous Flow [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3239-3245.
[15]	Huanqing Li, Zhaohua Chen, Zujia Chen, Qiwen Qiu, Youcai Zhang, Sihong Chen, Zhaoyang Wang. Research Progress in Mercury Ion Fluorescence Probes Based on Organic Small Molecules [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3067-3077.