SYNTHESIS OF α- HYDROXY-β, γ-UNSATURATED ESTERS

HClO4-SiO2 CATALYZED ISOMERISATION OF GLYCIDIC ESTERS TO α-HYDROXY- β, γ-UNSATURATED ESTERS

Authors

  • Lokesh Babu Jarugu Syngene International (India)
  • Yashwanth D. Vankar Indian Institute of Technology Kanpur
  • Anita Brar Govt. College of Engineering and Technology (Jammu - India)

DOI:

https://doi.org/10.51611/iars.irj.v12i02.2022.212

Keywords:

α-hydroxy-β, γ-unsaturated esters, glycidic esters, ionic liquid, per-chloric acid

Abstract

α-hydroxy-β, γ-unsaturated esters are important building blocks of bioactive compounds, natural products, achiral and chiral vinyl epoxides. These could be easily obtained by isomerization of glycidic esters. In this paper we have reported easy and convenient way of synthesis of α-hydroxy-β, γ-unsaturated esters by isomerisation of glycidic esters using inexpensive catalyst HClO4-SiO2 and eco-friendly ionic liquid. Moderate to good yields with lower reaction times reported.

Downloads

Download data is not yet available.

References

Downing, D. T. Rev. Pure. Appl. Chem. 1961, 11, 196.

Walba, D. M.; Eidman., K. F.; Haltiwanger, B. C. J. Org. Chem. 1989, 54, 4939.

Troast, B. M.; Tenaglia, A. Tetrahedron 1989, 45, 3021. (b) Stork, G.; Kobayashi, Y.; Suzuki, T.; Zhao, K. J. Am. Chem. Soc. 1990, 112, 1661. (c) Nicolaou, K. C.; Prasad, C. V.; Somer, P. K.; Hwang, C. K. J. Am. Chem. Soc. 1989, 111, 5335.(d) Corey, E. J.; Clark, D. A.; Goto, G.; Marfar, A.; Mioskowski, C.; Samuelson, B., Hammerstrom, S. J. Am. Chem. Soc. 1980, 102, 1436. ( e ). Bates, R. W.; Fernandez, M.; Ley, S. V. Tetrahedron 1991, 47, 9929.

Camps, F.; Castells, J.; Pascual, J. J. Org. Chem. 1996, 36, 3510.

Hartman, B. C.; Rickborn, B. J. Org. Chem. 1972, 37, 943.

Vankar, Y. D.; Choudhury, N. C.; Vankar, P. S. J. Chem. Res. 1989, 178.

Ourari, A.; Condom, R.; Guedj, R. Can. J. Chem. 1982, 60, 2707.

Ram Reddy, M. V.; Sangeeta, P. V.; Bhattacharya, I.; Vankar, Y. D. Synlett 1996, 241.

Chakraborthy, A. K.; Gulhane, R. Chem. Commun. 2003, 1896.

Welton, T. Chem. Rev. 1999, 99, 2071. (b) Wassersheild, P.; Keim, W. Angew. Chem. Int. Ed. Engl. 2000, 39, 3772.

Crossref Crossmark

Published

2022-08-29

Issue

Section

Peer Reviewed Research Manuscript

How to Cite

“SYNTHESIS OF α- HYDROXY-β, γ-UNSATURATED ESTERS: HClO4-SiO2 CATALYZED ISOMERISATION OF GLYCIDIC ESTERS TO α-HYDROXY- β, γ-UNSATURATED ESTERS” (2022) IARS’ International Research Journal, 12(02). doi:10.51611/iars.irj.v12i02.2022.212.

Citations