Abstract
Dealkylation of esters to carboxylic acids was performed using chloroaluminate ionic liquids (PyHBr/AlCl3, PyHCl/AlCl3, Me3NHCl/AlCl3, Et3NHCl/AlCl3) as catalyst and medium. The catalytic activity of PyHBr/AlCl3 (X(AlCl3) = 0.67) proved to be superior to the other three ionic liquids for the dealkylation of methyl benzoate with a conversion of 97% after 3 h at 140 °C. After easy separation from the products the ionic liquid PyHBr/AlCl3 could be reused six times without loss of its activity.
Graphical abstract
Similar content being viewed by others
References
Evans DA, Ripin DHB, Halstead DP, Campos KR (1999) J Am Chem Soc 121:6816
Sajiki H, Kuno H, Hirota K (1998) Tetrahedron Lett 39:1727
Chakraborti AK, Singh B, Chankeshwara SV, Patel AR (2009) J Org Chem 74:5967
Chakraborti AK, Basak A, Grover V (1999) J Org Chem 64:8014
Yates K, McClelland RA (1967) J Am Chem Soc 89:2686
Kirsch JF, Jencks WP (1964) J Am Chem Soc 86:833
Cossy J, Albouy S, Scheloske M, Pardo DG (1994) Tetrahedron Lett 35:1539
Taschner E, Liberek B (1956) Roczniki Chem 30:323
Kristensen J, Lawesson SO (1979) Tetrahedron 35:2075
Yasushi Y, Hideak S, Yoshitaka H (1996) J Organomet Chem 509:119
Marija L, Ivica C, Mladen L, Anamarija B, Vladimir V (2007) Croat Chem Acta 80:109
Apurba B, Nitin CP, Tomas V, Ritesh T, Gaurang P, Jiejun W (2006) Tetrahedron Lett 47:565
Strazzolini P, Scuccato M, Giumanini AG (2000) Tetrahedron 56:3625
Manabu N, Kiyoharu N, Midori S, Kaoru F, Eiichi F (1981) J Org Chem 46:1991
Wu YQ, Limburg DC, Wilkinson DE, Vaal MJ, Hamilton GS (2000) Tetrahedron Lett 41:2847
Chakraborti AK, Sharma L, Nayak MK (2002) J Org Chem 67:2541
Sharma L, Nayak MK, Chakraborti AK (1999) Tetrahedron 55:9595
Nayak MK, Chakraborti AK (1998) Chem Lett 27:297
Chakraborti AK, Nayak MK, Sharma L (2002) J Org Chem 67:1776
Wasserscheid P, Keim W (2000) Angew Chem 112:3926
Wasserscheid P, Keim W (2000) Angew Chem Int End 39:3773
Castro CAN (2010) J Mol Liq 156:10
Wasserscheid P, Welton T (2003) Ionic liquids in synthesis. Wiley-VCH, Weinheim
Souza RF, Suarez PAZ (2002) Chem Rev 102:3667
Huddleston JG, Williams HD, Swatloski RP, Visser AE, Rogers RD (1999) Chem Commun 35:1765
Sheldon R (2001) Chem Commun 37:2399
Adams CJ, Earle MJ, Roberts G, Seddon KR (1998) Chem Commun 34:2097
Holbrey JD, Seddon KR (1999) Clean Prod Process 1:223
Zhang S, Zhang Q, Zhang ZC (2004) Ind Eng Chem Res 43:614
Esser J, Wasserscheid P, Jess A (2004) Green Chem 6:316
Carmichael AJ, Earle MJ, Holbrey JD, McCormac PB, Seddon KR (1999) Org Lett 1:997
Chakraborti AK, Roy SR, Kumar D, Chopra P (2008) Green Chem 10:1111
Sarkar A, Roy SR, Chakraborti AK (2011) Chem Commun 47:4538
Roy SR, Chakraborti AK (2010) Org Lett 12:3866
Chakraborti AK, Roy SR (2009) J Am Chem Soc 131:6902
Jitender MK, Sanjay K (2010) Monatsh Chem 141:561
Jhillu SY, Basi VSR, Maddi SR, Namelikonda N, Attaluri RP (2003) Eur J Org Chem 2003:1779
Qiao K, Deng YQ (2003) Tetrahedron Lett 44:2191
Mahesh KP, Swapnil SM, Manikrao MS (2001) Tetrahedron Lett 42:9285
Amit CK, Bhushan MK (2002) Synlett 2002:152
Jitendra RH, Susheel JN, Manikrao MS (2001) Tetrahedron Lett 42:1979
Carlos WL (1999) Tetrahedron Lett 40:2461
Susheel JN, Jitendra RH, Manikrao MS (2001) J Org Chem 66:8616
Boon JA, Levinsky JA, Pflug JL, Wilkes JS (1986) J Org Chem 51:480
Yin DH, Li CZ, Tao L, Yu NY, Hu S, Yin DL (2006) J Mol Catal A Chem 245:260
Kemperman GJ, Roeters TA, Hilberink PW (2003) Eur J Org Chem 2003:1681
Liu T, Hu TZ (2004) Synth Commun 34:3209
Huang MY, Wu JC, Shieu FS, Lin JJ (2009) Catal Commun 10:1747
Jain N, Kumar A, Chauhan S, Chauhan SMS (2005) Tetrahedron 61:1015
Masahiro R, Shinichiro Y, Kohei S, Naoya O, Masayoshi W (1993) Mater Res Soc Symp Proc 285:135
Wasserscheid P, Welton T (2002) Ionic liquids in synthesis. Wiley-VCH, Weinheim, p 18
Buckingham J (1982) Dictionary of organic compounds, 5th edn. Routledge, New York
Acknowledgments
We are grateful to the Nature Science Foundation of Hubei Province (No. 2007ABA279) and Foundation of Hubei Educational Commission (No. B20111702) for financial support.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Wei, BM., Zhang, ZY., Dai, ZQ. et al. Application of chloroaluminate ionic liquid as catalyst and medium for the dealkylation of esters. Monatsh Chem 142, 1029–1033 (2011). https://doi.org/10.1007/s00706-011-0560-0
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00706-011-0560-0