Abstract
The special features of the oxidation of furfural by aqueous hydrogen peroxide in the presence of vanadyl sulfate and ethanol has been studied for the first time. It has been established that this reaction proceeds with the formation of previously unknown oxidation products of furan compounds, one of which was isolated from the reaction mixture as the ethyl ester. It was established by spectral methods and qualitative reactions that this product is 5-ethoxycarbonyl-4-hydroxy-3-oxo-2(3H)-furanone.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
L. A. Badovskaya, V. M. Latashko, V. V. Poskonin, E. P. Grunskaya, Z. I. Tyukhteneva, S. G. Rudakova, S. A. Pestunova, and S. A. Sarkisyan, Khim. Geterotsikl. Soedin., 1194 (2002). [Chem. Heterocycl. Comp., 38, 1040 (2002)].
V. V. Poskonin, Dissertation for Doctor of Chemical Sciences, Krasnodar (2001).
V. V. Poskonin and L. A. Badovskaya, Khim. Geterotsikl. Soedin., 1462 (1991). [Chem. Heterocycl. Comp., 27, 1177 (1991)].
V. V. Poskonin, L. V. Povarova, and L. A. Badovskaya, Khim. Geterotsikl. Soedin., 633 (1996). [Chem. Heterocycl. Comp., 32, 543 (1996)].
V. V. Poskonin and L. A. Badovskaya, in Chemistry and Chemical Technology of Furan Compounds, Interuniversity Symposium, Krasnodar Polytechnic Institute, Krasnodar (1987), p. 38.
V. V. Poskonin, L. A. Badovskaya, E. P. Grunskaya, A. V. Sarkisyan, and L. V. Povarova, in Chemistry and Chemical Technology of Furan Compounds, Interuniversity Symposium, Kuban State Technological University, Krasnodar (1996), p. 56.
V. V. Poskonin and L. A. Badovskaya, Russian Pat. 1715806; Byull. Izobret., No. 4, 36 (1992).
V. V. Poskonin, L. A. Badovskaya, S. P. Gavrilova, and V. G. Kul’nevich, Zh. Org. Khim., 25, 1701 (1989).
V. V. Poskonin, and L. A. Badovskaya, Russian Pat. 1703647; Byull. Izobret., No. 1, 22 (1992).
V. V. Poskonin, L. V. Povarova, and L. A. Badovskaya, Khim. Geterotsikl. Soedin., 893 (1998). [Chem. Heterocycl. Comp., 34, 771 (1998)].
V. V. Poskonin, L. A. Badovskaya, and L. V. Povarova, Russian Pat. 12124508; Byull. Izobret., No. 1, 38 (1999).
N. K. Strizhov, V. V. Poskonin, and E. P. Kupina, Pishch. Tekhnol., No. 5–6, 29 (1999).
L. A. Badovskaya, Dissertation for Doctor of Chemical Sciences, Krasnodar (1982).
V. G. Kul’nevich and L. A. Badovskaya, Usp. Khim., 44, 1256 (1975).
W. A. Waters, Mechanism of Oxidation of Organic Compounds [Russian translation], Mir, Moscow (1966).
E. T. Denisov, N. I. Mitskevich, and V. E. Agabekov, Mechanism of Liquid-Phase Oxidation of Oxygen-Containing Compounds [in Russian], Nauka Tekhnika, Minsk (1975).
B. C. Gilbert, R. O. C. Norman, and R. C. Sealy, J. Chem. Soc., Perkin Trans. 2, 824 (1974).
F. Feigl, Spot Tests in Organic Analysis (Trans. by R. E. Oesper), Elsevier, New York (1960), 675 pp.
A. R. Katritzky and J. M. Lagowski, Heterocyclic Chemistry, John Wiley & Sons, New York (1960), 274 pp.
Y. S. Rao, Chem. Rev., 76, 625 (1976).
P. Bonchev, Complex Formation and Catalytic Activity [Russian translation], Mir, Moscow (1975), p. 126.
Yu. L. Spirin, V. K. Grishchenko, and G. I. Kochetova, Teor. Eksp. Khim., 8, 532 (1972).
Author information
Authors and Affiliations
Corresponding author
Additional information
__________
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 386–392, March, 2008.
Rights and permissions
About this article
Cite this article
Poskonin, V.V. Catalytic oxidation of furan and hydrofuran compounds 8. Synthesis of 5-ethoxycarbonyl-4-hydroxy-3-oxo-2(3H)-furanone by the oxidation of furfural in the system aqueous H2O2-VOSO4-ethanol. Chem Heterocycl Comp 44, 295–300 (2008). https://doi.org/10.1007/s10593-008-0043-3
Received:
Revised:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-008-0043-3