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Acetylation of alcohols and phenols with acetic anhydride under solvent-free conditions using an ionic liquid based on morpholine as a recoverable and reusable catalyst

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Abstract

Rapid and efficient acetylation of alcohols and phenols with acetic anhydride is performed in the presence of economical Brønsted acidic ionic liquids that bear a propanesulfonic acid group on a morpholinium cation as catalysts under solvent-free conditions. [MMPPA][HSO4] (N-methylmorpholinium propanesulfonic acid ammonium hydrogensulfate) was proven to be the most active catalyst, and after removal of water, it could be recycled and reused for up to four times without a noticeable decrease in catalytic activity.

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References

  1. Greene TW, Wuts PGM (1999) Protective groups in organic synthesis, 3rd edn. Wiley, New York

    Google Scholar 

  2. Sartori G, Ballini R, Bigi F, Bosica G, Maggi R, Righi P (2004) Chem Rev 104:199

    Article  CAS  Google Scholar 

  3. Hofle G, Steglich W, Vorbrüggen H (1978) Angew Chem Int Ed 17:569

    Article  Google Scholar 

  4. Yoon HJ, Lee SM, Kim JH, Cho HJ, Choi JW, Lee SH, Lee YS (2008) Tetrahedron Lett 49:3165

    Article  CAS  Google Scholar 

  5. Orita A, Tanahashi C, Kakuda A, Otera J (2000) Angew Chem Int Ed 39:2877

    CAS  Google Scholar 

  6. Lee SG, Park JH (2003) J Mol Catal A: Chem 194:49

    Article  CAS  Google Scholar 

  7. Heravi MM, Behbahani FK, Shoar RH, Oskooie HA (2006) Catal Commun 7:136

    Article  CAS  Google Scholar 

  8. Shivani R, Gulhane A, Chakraborti (2007) J Mol Catal A: Chem 264:208

  9. Jeyakumar K, Chand DK (2006) J Mol Catal A: Chem 255:275

    Article  CAS  Google Scholar 

  10. Kumareswaran R, Pachmuthu K, Vankar YD (2000) Synlett 11:1652

    Google Scholar 

  11. Chakraborti AK, Gulhane R (2003) Tetrahedron Lett 44:3521

    Article  CAS  Google Scholar 

  12. Chakraborti AK, Gulhane R (2003) Chem Commun 15:1896

    Article  Google Scholar 

  13. Bosco JWJ, Agrahari A, Saikia AK (2006) Tetrahedron Lett 47:4065

    Article  CAS  Google Scholar 

  14. Ahmed N, Van Lier JE (2006) Tetrahedron Lett 47:5345

    Article  CAS  Google Scholar 

  15. Wang WJ, Cheng WP, Shao LL, Yang JG (2008) Catal Lett 121:77

    Article  CAS  Google Scholar 

  16. Forsyth SA, MacFarlane DR, Thomson RJ, von Itzestein M (2002) Chem Commun 7:714

    Article  Google Scholar 

  17. Das B, Thirupathi P (2007) J Mol Catal A: Chem 269:12

    Article  CAS  Google Scholar 

  18. Moghadam M, Tangestaninejad S, Mirkhani V, Bltork IM, Taghavi SA (2007) J Mol Catal A: Chem 274:217

    Article  CAS  Google Scholar 

  19. Jin TS, Sun G, Li YW, Li TS (2002) Green Chem 4:255

    Article  CAS  Google Scholar 

  20. Kaizer J, Greczi Z, Speier G (2001) React Kinet Catal Lett 73:91

    Article  CAS  Google Scholar 

  21. Tale RH, Adude RN (2006) Tetrahedron Lett 47:7263

    Article  CAS  Google Scholar 

  22. Fang D, Luo J, Zhou XL, Ye ZW, Liu ZL (2007) J Mol Catal A: Chem 274:208

    Article  Google Scholar 

  23. Fang D, Gong K, Zhang DZ, Liu ZL (2009) Monatsh Chem 140:1325

    Article  CAS  Google Scholar 

  24. Yue CB, Mao AQ, Wei YY, Lü MJ (2008) Catal Commun 9:1571

    Article  CAS  Google Scholar 

  25. Yue CB, Wei YY, Lü MJ (2006) Chin J Appl Chem 23:1282

    Article  CAS  Google Scholar 

  26. Babasaheb PB, Neeta SJ, Vinod TK, Sanjay SS (2008) Aust J Chem 61:231

    Article  Google Scholar 

  27. Huang BH, Li ZJ, Wang YF, Shi N, Fang YX, Zhang K, Du ZY (2007) Chin Pat 200710029820.3

  28. Huang BH, Li ZJ, Shi N, Xu XL, Zhang K, Fang YX (2009) Chin J Org Chem 29:770

    Google Scholar 

  29. Qiu RH, Zhu YY, Xu XH, Li YH, Shao LL, Ren XF, Cai XT, An DL, Yin SF (2009) Catal Commun 10:1889

    Article  CAS  Google Scholar 

  30. Jin TS, Zhao Y, Liu LB, Chen Z, Li TS (2006) Synth Commun 36:1221

    Article  CAS  Google Scholar 

  31. Satam JR, Gawande MB, Deshpande SS, Jayaram RV (2007) Synth Commun 37:3011

    Article  CAS  Google Scholar 

  32. Schreyer RC (1952) J Am Chem Soc 74:3242

    Article  CAS  Google Scholar 

  33. Chattaway FD (1931) J Chem Soc 2495

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Acknowledgments

This study was performed under financial support from the SRTP of Anhui University of Technology (project no. 09016), the Key Project of the Scientific Research Foundation sponsored by the Education Department of Anhui Province, China (project no. KJ2010A339), and the Foundation for Young Talents in the College of Anhui Province, China (project no. 2010SQRL033ZD).

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Correspondence to Caibo Yue.

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Yue, C., Liu, Q., Yi, T. et al. Acetylation of alcohols and phenols with acetic anhydride under solvent-free conditions using an ionic liquid based on morpholine as a recoverable and reusable catalyst. Monatsh Chem 141, 975–978 (2010). https://doi.org/10.1007/s00706-010-0353-x

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  • DOI: https://doi.org/10.1007/s00706-010-0353-x

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