Abstract
The conditions for the oxidation of formylfurans with sodium hypobromite and hypochlorite that promote an increase in the yields for the furancarboxylic acids were investigated. The usual composition of the hypohalite mixture [NaOH]∶[X2] = 3 gives low yields of the furancarboxylic acids, particularly on the basis of 5-methylfurfural. Doubling the relative percentage of alkali promotes an increase in the efficiency of the reaction. An interpretation of the process is given.
Similar content being viewed by others
Literature cited
Yu. M. Shapiro, Khim. Geterotsikl. Soedin., No. 9, 1168 (1977).
V. I. Lutkova and N. I. Shmagina, Plast. Massy, No. 4, 56 (1960).
A. P. Salchinkin and L. B. Lapkova, Zh. Prikl. Khim., 28, 141 (1956).
N. K. Kochetkov and É. E. Nifant'eva, Vestn. Mosk. Gos. Univ., Ser. Mat., Mekhan., Astron., Fiz., Khim., No. 5, 119 (1958).
K. Yu. Novitskii, V. P. Volkov, and Yu. K. Yur'ev, Zh. Obshch. Khim., 32, 399 (1962).
R. Andrisano, Boll. Sci. Fac. Chim. Ind. Bologna, 7, 66 (1949).
T. Masamune, Bull. Chim. Soc. Jpn., 48, 491 (1975).
D. R. Kreile, V. A. Slavinskaya, L. Ya. Kruminya, D. Ya. Eglite, and D. É. Sile, USSR Inventor's Certificate No. 530881; Byull. Izobret., No. 37, 61 (1976).
Yu. A. Zhdanov and O. A. Pustovarova, Zh. Obshch. Khim., 37, 2780 (1967).
Yu. M. Shapiro and V. G. Kul'nevich, USSR Inventor's Certificate No. 519412; Byull. Izobret., No. 24, 69 (1976).
Syntheses of Heterocyclic Compounds [in Russian], Vol. 1, Izd. Akad. Nauk Arm. SSR, Yerevan (1956), pp. 30, 34, 36, 42.
A. J. Downs and C. J. Adams, The Chemistry of Chlorine, Bromine, Iodine, and Astatine, Pergamon Press, New York (1973), p. 1399.
Z. N. Nazarova, Zh. Org. Khim., 10, 1341 (1974).
Author information
Authors and Affiliations
Additional information
See [1] for Communication 1.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1463–1467, November, 1982.
Rights and permissions
About this article
Cite this article
Shapiro, Y.M., Pustovarova, O.A., Baum, É. et al. Reactions of aldehydes of the furan series. 2. Oxidation with sodium hypohalites. Chem Heterocycl Compd 18, 1132–1136 (1982). https://doi.org/10.1007/BF00506357
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00506357