Skip to main content
SpringerLink
Log in

Lewis basic ionic liquid as an efficient and facile catalyst for acetylation of alcohols, phenols, and amines under solvent-free conditions

  • Original Paper
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

The Lewis basic ionic liquid 1,8-diazabicyclo[5.4.0]undec-7-en-8-ium acetate was employed for the acetylation of various phenols, alcohols, and amines in good-to-excellent yields at 50 °C under solvent-free conditions in a short time. Compared with existing methods based on conventional catalysts and toxic solvents, the reported method is simple, mild and environmentally viable. Furthermore, the ionic liquid was conveniently separated from the products and easily recycled to catalyze other acetylation reactions with excellent yields.

Graphical abstract

.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Scheme 1
Scheme 2

Similar content being viewed by others

References

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

  2. Hanson JR (1999) Protective groups in organic synthesis. Blackwell, Malden

  3. Steglich W, Hofle G (1969) Angew Chem Int Ed 8:981

    Article  CAS  Google Scholar 

  4. Vedejs E, Bennett NS, Conn LM, Diver ST, Gingras M, Lin S, Oliver PA, Peterson MJ (1993) J Org Chem 58:7286

    Article  CAS  Google Scholar 

  5. Torregiani E, Seu G, Minassi A, Appendino G (2005) Tetrahedron Lett 46:2193

    Article  CAS  Google Scholar 

  6. Bhattacharya AK, Diallo MA, Ganesh KN (2008) Synth Commun 38:1518

    Article  CAS  Google Scholar 

  7. Meshram G, Patil VD (2009) Synth Commun 39:4384

    Article  CAS  Google Scholar 

  8. Chakraborti AK, Gulhane R (2004) Synlett 15:627

    Article  Google Scholar 

  9. Chakraborti AK, Gulhane R (2003) Tetrahedron Lett 44:6749

    Article  CAS  Google Scholar 

  10. Kamal A, Khan MNA, Reddy KS, Srikanth YVV, Krishnaji T (2007) Tetrahedron Lett 48:3813

    Article  CAS  Google Scholar 

  11. Shirini F, Zolfigol MA, Aliakbar AR, Albadi J (2010) Synth Commun 40:1022

    Article  CAS  Google Scholar 

  12. Bartoli G, Bosco M, Dalpozzo R, Marcantoni E, Massaccesi M, Sambri L (2003) Eur J Org Chem 4611

  13. Chakraborti AK, Sharma L, Gulhane R, Shivani (2003) Tetrahedron 59:7661

    Google Scholar 

  14. Chakraborti AK, Gulhane R, Shivani (2003) Synlett 1805

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

    Article  CAS  Google Scholar 

  16. Chakraborti AK, Gulhane R, Shivani (2004) Synthesis 111

  17. Chakraborti AK, Shivani (2006) J Org Chem 71:5785

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

    Article  CAS  Google Scholar 

  19. Hajipour AR, Khazdooz L, Ruoho AE (2009) J Chin Chem Soc 56:398

    CAS  Google Scholar 

  20. Yue CB, Liu QQ, Yi TF, Chen Y (2010) Monatsh Chem 141:975

    Article  CAS  Google Scholar 

  21. Ballini R, Bosica G, Carloni S, Ciaralli L, Maggi R, Sartori G (1998) Tetrahedron Lett 39:6049

    Article  CAS  Google Scholar 

  22. Kumareswaran R, Pachamuthu K, Vankar YD (2000) Synlett 1652

  23. Chakraborti AK, Gulhane R (2003) Chem Commun 1896

  24. Birman VB, Li XM, Han ZF (2007) Org Lett 9:37

    Article  CAS  Google Scholar 

  25. Yang X, Birman VB (2009) Org Lett 11:1499

    Article  CAS  Google Scholar 

  26. Ying AG, Liu L, Wu GF, Chen G, Chen XZ, Ye WD (2009) Tetrahedron Lett 50:1653

    Article  CAS  Google Scholar 

  27. Ying AG, Wang LM, Wang LL, Chen XZ, Ye WD (2010) J Chem Res 30

  28. Yang ZZ, He LN, Miao CX, Chanfreau S (2010) Adv Synth Catal 352:2233

    Article  CAS  Google Scholar 

  29. Das R, Chakraborty D (2011) Synthesis 1621

  30. Simion AM, Hashimoto I, Mitoma Y, Egashira N, Simion C (2011) Synth Commun 42:921

    Article  Google Scholar 

  31. Neuvonen H, Neuvonen K, Koch A, Kleinpeter E, Pasanen P (2002) J Org Chem 67:6995

    Article  CAS  Google Scholar 

  32. Zarei A, Hajipour AR, Khazdooz L (2011) Synth Commun 41:1772

    Article  CAS  Google Scholar 

  33. Iuchi Y, Obora Y, Ishii Y (2010) J Am Chem Soc 132:2536

    Article  CAS  Google Scholar 

  34. Chakraborti AK, Singh B, Chankeshwara SV, Patel AR (2009) J Org Chem 74:5967

    Article  CAS  Google Scholar 

  35. Tanoue Y, Hamada M, Kai N, Nagai T, Sakata K, Hashimoto M, Morishita SI (2000) J Heterocycl Chem 37:1351

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  37. Dubovyk I, Watson IDG, Yudin AK (2007) J Am Chem Soc 129:14172

    Article  CAS  Google Scholar 

  38. Grugel H, Minuth T, Boysen MMK (2010) Synthesis 3248

  39. Barbero M, Bazzi S, Cadamuro S, Dughera S (2009) Eur J Org Chem 430

  40. Lee YM, Moon ME, Vajpayee V, Filimonov VD, Chi KW (2010) Tetrahedron 66:7418

    Article  CAS  Google Scholar 

  41. dos Santos CMG, McCabe T, Watson GW, Kruger PE, Gunnlaugsson T (2008) J Org Chem 73:9235

    Article  Google Scholar 

  42. Karimi B, Behzadnia H (2010) Synlett 2019

  43. Strekowski L, Patterson SE, Janda L, Wydra RL, Harden DB, Lipowska M, Cegla MT (1992) J Org Chem 57:196

    Article  CAS  Google Scholar 

  44. Bedford RB, Engelhart JU, Haddow MF, Mitchell CJ, Webster RL (2010) Dalton Trans 39:10464

    Article  CAS  Google Scholar 

  45. Liu LF, Liu H, Pi HJ, Yang S, Yao M, Du WT, Deng WP (2011) Synth Commun 41:553

    Article  CAS  Google Scholar 

  46. Kajihara K, Arisawa N, Shuto S (2008) J Org Chem 73:9494

    Article  CAS  Google Scholar 

  47. Shing TKM, Li TY, Kok SHL (1999) J Org Chem 64:1941

    Article  CAS  Google Scholar 

  48. Xu SJ, Held I, Kempf B, Mayr H, Steglich W, Zipse H (2005) Chem Eur J 11:4751

    Article  CAS  Google Scholar 

Download references

Acknowledgments

We thank the National Natural Science Foundations of China (21076183, 21006087) for financial support.

Author information

Authors and Affiliations

  1. Department of Chemical and Biological Engineering, Zhejiang University, Hangzhou, 310027, People’s Republic of China

    Li Ji, Chao Qian & Xin-zhi Chen

Authors
  1. Li Ji
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Chao Qian
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Xin-zhi Chen
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Chao Qian.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOC 81 kb)

Rights and permissions

Reprints and permissions

About this article

Cite this article

Ji, L., Qian, C. & Chen, Xz. Lewis basic ionic liquid as an efficient and facile catalyst for acetylation of alcohols, phenols, and amines under solvent-free conditions. Monatsh Chem 144, 369–374 (2013). https://doi.org/10.1007/s00706-012-0820-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-012-0820-7

Keywords

Search

Navigation