Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Direct Coupling of Cs2CO3 and Alcohols for the Synthesis of Dimethyl, Diethyl, and Various Dialkyl Carbonates

  • Lim, Yu Na (Division of Energy Systems Research, Ajou University) ;
  • Wang, Xi (Division of Energy Systems Research, Ajou University) ;
  • Park, Eun-Jin (Division of Energy Systems Research, Ajou University) ;
  • Jang, Hye-Young (Division of Energy Systems Research, Ajou University)
  • Received : 2013.09.18
  • Accepted : 2013.11.09
  • Published : 2014.02.20
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Abstract

Keywords

Experimental

Representative Procedure for Carbonates Synthesis from Cs2CO3. A mixture of cinnamyl alcohol (67.1 mg, 0.5 mmol), Cs2CO3 (325.8 mg, 1 mmol) and 1-n-butyl-3-methylimidazolium hexafluorophosphate (bmimPF6) (0.1 mL) in dibromomethane (1 mL) was equipped with a seal tube and stirred for 18 h at 70 ℃. The reaction mixture was evaporated and purified by flash column chromatography (silica gel) (2% Ether/hexane) to obtain dicinnamyl carbonate (1) 69.0 mg (94%).

Representative Procedure for Synthesis of Low-molecular-weight Carbonates (DMC and DEC). A mixture of methanol (16.0 mg, 0.5 mmol), Cs2CO3 (325.8 mg, 1 mmol), 1-n-butyl-3-methylimidazolium hexafluorophosphate(bmimPF6) (0.1 mL) and tetradecane (19.8 mg, 0.1 mmol) in dibromomethane (1 mL) was equipped with a seal tube and stirred for 18 h at 70 ℃. The yield was determined by GC analysis of the reaction mixture using tetradecane as an internal standard; average of three runs.

References

  1. (a) Shaikh, A.-A. G. Chem. Rev. 1996, 96, 951-976. https://doi.org/10.1021/cr950067i
  2. (b) Pacheco, M. A.; Marshall, C. L. Energ. Fuels 1997, 11, 2-29. https://doi.org/10.1021/ef9600974
  3. (c) Ono, Y. Appl. Catal. A: General 1997, 155, 133-166. https://doi.org/10.1016/S0926-860X(96)00402-4
  4. (d) Sakakura, T.; Choi, J.-C.; Yasuda, H. Chem. Rev. 2007, 107, 2365-2387. https://doi.org/10.1021/cr068357u
  5. (e) Aresta, M.; Dibenedetto, A. Dalton Trans. 2007, 2975-2992.
  6. (f) Sakakura, T.; Kohno, K. Chem. Commun. 2009, 1312-1330.
  7. (g) Mikkelsen, M.; Jørgensen, M.; Krebs, F. C. Energy Environ. Sci. 2010, 3, 43-81. https://doi.org/10.1039/b912904a
  8. (a) Fukuoka, S.; Kawamura, M.; Komiya, K.; Tojo, M.; Hachiya, H.; Hasegawa, K.; Aminaka, M.; Okamoto, H.; Fukawa, I.; Konno, S. Green Chem. 2003, 5, 497-507. https://doi.org/10.1039/b304963a
  9. (b) Sankar, M.; Satv, S.; Manikandan, P. ChemSusChem. 2010, 3, 575-578. https://doi.org/10.1002/cssc.201000038
  10. (c) Yang, Z.-Z.; He, L.-N.; Dou, X.-Y.; Chanfreau, S. Tetrahedron Lett. 2010, 51, 2931-2934. https://doi.org/10.1016/j.tetlet.2010.03.114
  11. (d) Wang, L.; Wang, Y.; Liu, S.; Lu, L.; Ma, X.; Deng, Y. Catal. Commun. 2011, 16, 45-49. https://doi.org/10.1016/j.catcom.2011.09.004
  12. (e) Wang, J.-Q.; Sun, J.; Cheng, W.-G.; Shi, C.-Y.; Dong, K.; Zhang, X.-P.; Zhang, S.-J. Catal. Sci. & Technol. 2012, 2, 600-605. https://doi.org/10.1039/c1cy00342a
  13. (a) Kizlink, J.; Pastucha, I. Collect. Czech. Chem. Commun. 1995, 60, 687-692. https://doi.org/10.1135/cccc19950687
  14. (b) Sakakura, T.; Saito, Y.; Okano, M.; Choi, J.-C.; Sako, T. J. Org. Chem. 1998, 63, 7095-7096. https://doi.org/10.1021/jo980460z
  15. (c) Choi, J.-C.; He, L.-N.; Yasuda, H.; Sakakura, T. Green Chem. 2002, 4, 230-234. https://doi.org/10.1039/b200623p
  16. (d) Choi, J.-C.; Kohno, K.; Ohshima, Y.; Yasuda, H.; Sakakura, T. Catal. Commun. 2008, 9, 1630-1633. https://doi.org/10.1016/j.catcom.2008.01.013
  17. (e) Stoian, D. C.; Taboada, E.; Llorca, J.; Molins, E.; Median, F.; Segarra, A. M. Chem. Commun. 2013, 49, 5489-5491. https://doi.org/10.1039/c3cc41298a
  18. (a) Mucciante, V.; Rossi, L.; Feroci, M.; Sotgiu, G. Synth. Commun. 2002, 32, 1205-1210. https://doi.org/10.1081/SCC-120003611
  19. (b) Cella, J. A.; Bacon, S. W. J. Org. Chem. 1984, 49, 1122-1125. https://doi.org/10.1021/jo00180a033
  20. (c) Verdecchia, M.; Feroci, M.; Palombi, L.; Rossi, L. J. Org. Chem. 2002, 67, 8287-8289. https://doi.org/10.1021/jo0259461
  21. (d) Jorapur, Y. R.; Chi, D. Y. J. Org. Chem. 2005, 70, 10774-10777. https://doi.org/10.1021/jo051722h
  22. (e) Chu, F.; Dueno, E. E.; Jung, K. W. Tetrahedron Lett. 1999, 40, 1847-1850. https://doi.org/10.1016/S0040-4039(99)00084-2
  23. (a) McGhee, W.; Riley, D. J. Org. Chem. 1995, 60, 6205-6207. https://doi.org/10.1021/jo00124a044
  24. (b) Fang, S.; Fujimoto, K. Appl. Catal., A 1996, 142, L1-L3. https://doi.org/10.1016/0926-860X(96)00081-6
  25. (c) Chu, F.; Dueno, E. E.; Jung, K. W. Tetrahderon Lett. 1999, 40, 1847-1850. https://doi.org/10.1016/S0040-4039(99)00084-2
  26. (d) Kim, S.-J.; Chu, F.; Dueno, E. E.; Jung, K. W. J. Org. Chem. 1999, 64, 4578-4579. https://doi.org/10.1021/jo990520g
  27. (e) Isaacs, N. S.; O'Sullivan, B.; Verhaelen, C. Tetrahedron 1999, 55, 11949-11956. https://doi.org/10.1016/S0040-4020(99)00693-6
  28. (f) Salvatore, R. N.; Flanders, V. L.; Ha, D.; Jung, K. W. Org. Lett. 2000, 2, 2797-2800. https://doi.org/10.1021/ol006212i
  29. (g) Fujita, S.-i.; Bhanage, B. M.; Ikushima, Y.; Arai, M. Green Chem. 2001, 3, 87-91. https://doi.org/10.1039/b100363l
  30. (h) Zhang, L.; Niu, D.; Zhang, K.; Zhang, G.; Luo, Y.; Lu, J. Green Chem. 2008, 10, 202-206. https://doi.org/10.1039/b711981j
  31. (a) Kadokawa, J.-I.; Habu, H.; Fukamachi, S.; Karasu, M.; Tagaya, H.; Chiba, K. J. Chem. Soc., Perkin Trans. 1 1999, 2205-2208.
  32. (b) Bratt, M. O.; Taylor, P. C. J. Org. Chem. 2003, 68, 5439-5444. https://doi.org/10.1021/jo026753g
  33. (c) Yamazaki, Y.; Kakuma, K.; Du, Y.; Saito, S. Tetrahedron 2010, 66, 9675-9680. https://doi.org/10.1016/j.tet.2010.10.051
  34. Galli, C. Org. Prep. Proceed. Int. 1992, 24, 285-307. https://doi.org/10.1080/00304949209355891
  35. Jorapur, Y. R.; Chi, D. Y. J. Org. Chem. 2005, 70, 10774-10777. https://doi.org/10.1021/jo051722h

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