SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2013 , Vol. 33 >Issue 01: 190 - 194

DOI: https://doi.org/10.6023/cjoc201208010

Notes

Cesium Chloride Catalysized the Reaction of Sodium (Potassium) Carboxylates with Alkyl Bromides (Chlorides)

  • Liu Wenqi ,
  • Qi Jianyong ,
  • Chen Jinyang ,
  • Li Ningbo ,
  • Qui Renhua ,
  • Xu Xinhua
Expand
  • a Hunan Provincial Key Laboratory of Xiangnan Rare-Precious Metals Compounds Research and Application, Xiangnan University, Chenzhou 42300;
    b College of Chemistry Chemical and Engineering, Hunan University, Changsha 410082

Received date: 2012-08-13

  Revised date: 2012-09-08

  Online published: 2012-09-21

Supported by

Project supported by the Natural Science Foundation of Hunan Province (No. 08JJ3018).

Fold

Abstract

In the presence of catalytic amounts of cesium chloride, using DMF as solvent, sodium (potassium) carboxylates reacted with α-chloroacetates at room temperature or reacted with alkyl bromides (chlorides) at 60℃ to give the corresponding (α-alkoxyformacyl)methyl carboxylic esters and carboxylic esters in >90% yields. The catalytic mechanism was discussed.

Key words： cesium chloride; sodium (potassium) carboxylates; alkyl bromides (chlorides); esterification

Cite this article

Liu Wenqi , Qi Jianyong , Chen Jinyang , Li Ningbo , Qui Renhua , Xu Xinhua . Cesium Chloride Catalysized the Reaction of Sodium (Potassium) Carboxylates with Alkyl Bromides (Chlorides)[J]. Chinese Journal of Organic Chemistry, 2013 , 33(01) : 190 -194 . DOI: 10.6023/cjoc201208010

References

[1] Tzalis, D.; Knochel, P. Angew. Chem., Int. Ed. 1999, 38, 1463.

[2] Salvatore, R. N.; Nagle, A. S.; Jung, K. W. J. Org. Chem. 2002, 67, 674.

[3] Tzalis, D.; Koradin, C.; Knochel, P. Tetrahedron Lett. 1999, 40, 6193.

[4] Li, X. W.; Liu, W. Q.; Zou, K. B. Chin. J. Org. Chem. 2007, 27, 1176 (in Chinese). (黎小武, 刘文奇, 邹康兵, 许新华, 有机化学, 2007, 27, 1176.)

[5] Xia, X.; Zou, K. B.; Fang, D. W.; Xu, X. H. Chin. J. Org. Chem. 2008, 28, 1487 (in Chinese). (夏湘, 邹康兵, 方大为, 许新华, 有机化学, 2008, 28, 1487.)

[6] Zou, K. B.; Qiu, R. H.; Fang, D. W.; Liu, X. Y.; Xu, X. H. Synth. Commun. 2008, 38, 237.

[7] Zou, K. B.; Yin, X. H.; Liu, W. Q.; Qiu, R. H.; Li, L. X.; Shao, L. L.; Li, Y. H.; Xu, X. H.; Yang, R. H. Synth. Commun. 2009, 39, 646.

[8] Xia, X.; Zou, K. B.; Li, N. X.; Zhang, Z. Y.; Shao, L. L.; Xu, X. H. Acta Chim. Sinica 2008, 66, 1749. (夏湘, 邹康兵, 李诺信, 张尊英, 邵玲玲, 许新华, 化学学报, 2008, 66, 1749.)

[9] Steven, C. W.; Rayman, Y. W. Tetrahedron Lett. 1972, 13, 1853.

[10] Douglas, J. R.; Patrick, G.; Albert, O. B. J. Org. Chem. 1979, 44, 1149.

[11] Zaher, M. A. J.; Hao, Y. S.; Bun, C. C. Tetrahedron Lett. 2002, 43, 9381.

[12] Cheng, B. C.; Xie, W. L. J. Central South Univ. Technol. 1998, 29, 401 (in Chinese). (成本诚, 谢文林, 中南工业大学学报, 1998, 29, 401.)

[13] Chen, D. M.; Yang, H. R.; Li, B. N. Petrochem. Technol. 1999, 28, 528 (in Chinese). (陈达美, 杨辉荣, 黎碧娜, 石油化工, 1999, 28, 5.)

[14] Barratt, B. J. W.; Easton, C. J.; Simpson, J. S. PCT Int. Appl. 2004, 47, 87.

[15] Nielsen, N. M.; Bundgaard, H. Int. J. Pharm. 1987, 391, 75.

[16] Murai, K.; Akazome, G. Kogyo Kagaku Zasshi 1959, 62, 1094.

[17] Liu, Y.; Wei, M.; Liu, Z.-D. China Food Additives 2011, 4, 8.

[18] Sadieva, N. F.; Iskenderova, S. A.; Agaev, B. K.; Magerramova, S. N. Azerb. Khim. Zh. 2010, (4), 68.

[19] Nudelman, N. S.; Mendiara, S. Tetrahedron Lett. 1997, 38(13), 2245.

[20] Long, L.-P.; Zhong, T.-S.; Ding, L.-Z.; Yu, S.-X. Chin. J. Synth. Chem. 2002, 10(6), 542.

[21] Vijayakumar, B.; Nagendrappa, G.; Prakash, B. S. J. Indian J. Chem. Technol. 2009, 16(5), 377.

[22] Zhang, M.; Hanson, P. R. Sci. Synth. 2006, 20, 863.

Options
Outlines

/

〈 〉