Ionic liquid as Green solvent for ?-alkylation of Active Methyelne Compounds

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Ionic liquid as Green solvent for ?-alkylation of Active Methyelne Compounds

Geeta Kotian

Author Affiliations

¹Department of Chemistry, St. Xavier’s, Autonomous, College, Mumbai 400 001, INDIA

Res.J.chem.sci., Volume 5, Issue (5), Pages 85-88, May,18 (2015)

Abstract

A selective monoalkylation of active methylene compounds with various alkyl halides in 1-butyl-3-methylimidazolium hexafluorophosphate [bmim] [PF₆] ionic liquid is reported here. The product can be recovered by vacuum distillation and the ionic liquid can be recycled without any loss in yield.

References

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Khadilkar B.M and Rebeiro G.L., Benzoylation in room temperature ionic liquids, Synth. Commun.,30, 1605 (2000)
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Khadilkar B.M and Rebeiro G.L., Chloroaluminate ionic liquid for Fischer indole synthesis, Synthesis, 370 (2001)
Khadilkar B.M and Khandekar A.C., Pechmann Reaction in Chloroaluminate Ionic Liquid, Synlet, 152 (2002)
Earle M.J., McCormac P.B and Seddon K.R., Regioselective alkylation in ionic liquids, J. Chem. Soc., Chem. Commun., 2245 (1998)
Wheeler C., West K.N., Liotta C.L and Eckert C.A., Ionic liquids as catalytic green solvents for nucleophilic displacement reactions, J. Chem. Soc., Chem. Commun., 887 (2001)
Ratti R., Use of Non-Conventional Reaction Media: A Green Approach, Res. J. Chem. Sci., 5(3), 77-89 (2015)
Gogoi S., Enzymatic Bioconversion in Non-conventional Media, Res.J.chem.sci., 4(11), 103-116 (2014)
Mohd S., Sayyed H. , Sayyed A. , Pradhan V. and Mazahar F., Thermodynamic Characteristics of Solvents: A Review, Res. J. chem. sci., 3(11), 98-104 (2013)
Dharaskar S.A., Ionic Liquids (A Review): The Green Solvents for Petroleum and Hydrocarbon Industries, Res. J. chem. sci., 2(8), 80-85 (2012)
Starks C.L., Liotta C. L and Halpern M., Phase-transfer catalysis reactions with strong bases. Phase Transfer Catalysis, Chapman and Hall, London, 383 (1994)
Cope A.C., Holmes H.L and House, H.O., The alkylation of esters and nitriles. Organic Reactions, John Wiley and Sons, New York, 107 (1957)
Masamune S., Phase-transfer alkylation of nitriles: phenylbutyronitrile, Organic Synthesis, ed., John Wiley and Sons, New York, 55, 91 (1976)
Huddleston J.G., Willauer H. D., Swatloski R.P., Visser A.E and Rogers R.D., Room temperature ionic liquids as novel media for ‘clean’ liquid-liquid extraction, J. Chem. Soc., Chem. Commun., 1765 (1998)
Khadilkar B.M and Rebeiro G.L., Microwave assisted synthesis of room temperature ionic liquid precursors in closed vessel, Organic Process Research and Development,6(6), 826 (2002)

[ref1] Adams C.H., Earle M.J. Roberts G and Seddon K.R., Friedel-Crafts reactions in room temperature ionic liquids, J. Chem. Soc., Chem. Commun., 2097, (1998)

[ref2] Khadilkar B.M and Rebeiro G.L., Benzoylation in room temperature ionic liquids, Synth. Commun.,30, 1605 (2000)

[ref3] Saurez P.A.Z., Dulluis J.E.L., Einloft S., De Souza R.F and Dupont J., The use of new ionic liquids in two-phase catalytic hydrogenation reaction by rhodium complexes, Polyhedron, 15, 1217 (1996)

[ref4] Virginie Le B and Rene G., J. Chem. Soc., Chem. Commun., 22, 2195 (2000)

[ref5] Khadilkar B.M and Rebeiro G.L., Chloroaluminate ionic liquid for Fischer indole synthesis, Synthesis, 370 (2001)

[ref6] Khadilkar B.M and Khandekar A.C., Pechmann Reaction in Chloroaluminate Ionic Liquid, Synlet, 152 (2002)

[ref7] Earle M.J., McCormac P.B and Seddon K.R., Regioselective alkylation in ionic liquids, J. Chem. Soc., Chem. Commun., 2245 (1998)

[ref8] Wheeler C., West K.N., Liotta C.L and Eckert C.A., Ionic liquids as catalytic green solvents for nucleophilic displacement reactions, J. Chem. Soc., Chem. Commun., 887 (2001)

[ref9] Ratti R., Use of Non-Conventional Reaction Media: A Green Approach, Res. J. Chem. Sci., 5(3), 77-89 (2015)

[ref10] Gogoi S., Enzymatic Bioconversion in Non-conventional Media, Res.J.chem.sci., 4(11), 103-116 (2014)

[ref11] Mohd S., Sayyed H. , Sayyed A. , Pradhan V. and Mazahar F., Thermodynamic Characteristics of Solvents: A Review, Res. J. chem. sci., 3(11), 98-104 (2013)

[ref12] Dharaskar S.A., Ionic Liquids (A Review): The Green Solvents for Petroleum and Hydrocarbon Industries, Res. J. chem. sci., 2(8), 80-85 (2012)

[ref13] Starks C.L., Liotta C. L and Halpern M., Phase-transfer catalysis reactions with strong bases. Phase Transfer Catalysis, Chapman and Hall, London, 383 (1994)

[ref14] Cope A.C., Holmes H.L and House, H.O., The alkylation of esters and nitriles. Organic Reactions, John Wiley and Sons, New York, 107 (1957)

[ref15] Masamune S., Phase-transfer alkylation of nitriles: phenylbutyronitrile, Organic Synthesis, ed., John Wiley and Sons, New York, 55, 91 (1976)

[ref16] Huddleston J.G., Willauer H. D., Swatloski R.P., Visser A.E and Rogers R.D., Room temperature ionic liquids as novel media for ‘clean’ liquid-liquid extraction, J. Chem. Soc., Chem. Commun., 1765 (1998)

[ref17] Khadilkar B.M and Rebeiro G.L., Microwave assisted synthesis of room temperature ionic liquid precursors in closed vessel, Organic Process Research and Development,6(6), 826 (2002)