Conclusions
-
1.
The method presented for oxidation of aromatic aldehydes and alcohols by oxygen in KOH-DME systems makes it possible to obtain carboxylic acids in high yields under mild conditions.
-
2.
The rate of oxidation of alcoholates varies greatly according to the nature of the accompanying action and decreases in the order: K+ > Na+ > L+.
Similar content being viewed by others
Literature cited
E. Müller (ed), Houben-Weyl's Methoden der Organishen Chemie, B, Vol. 6, Part 2, Georg Thieme Verlag, Stuttgart (1963), pp. 68–70.
J. Dumas and J. S. Stass, Ann. Chem.,35, 129 (1840).
R. A. Dytham and B. C. L. Weidom, Tetrahedron,8, 246 (1960).
S. V. Vitt and N. S. Martinkova, Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, 1125 (1962).
S. V. Vitt and N. S. Martinkova, Izv. Akad. Nauk SSSR, Ser. Khim., 524 (1964).
A. BrÄndström, Ark. Kemi,11, 567 (1957).
J. Barthel, G. Schwitzgebel, and R. Z. Wachter, Z. Phys. Chem.,55, 331 (1967).
J. H. Exner and E. G. Steener, J. Am. Chem. Soc.,96, 1782 (1974).
G. A. Graze and J. Watt, Tetrahedron Lett.,23, 975 (1982).
E. W. Warnhoff, P. Reynolds-Warnhoff, and J. H. Wong, J. Am. Chem. Soc.,102, 5956 (1980).
P. T. Lansbury and F. D. Salva, J. Am. Chem. Soc.,89, 1890 (1967).
W. N. Olmstead, Z. Margolin, and F. G. Bordwell, J. Org. Chem.,45, 3295 (1980).
E. M. Arnett and L. E. Small, J. Am. Chem. Soc.,99, 808 (1977).
I. P. Beletskaya, A. A. Grinfel'd, and G. A. Artamkina, Izv. Akad. Nauk SSSR, Ser. Khim., 2836 (1981).
E. C. Ashby, A. B. Goel, and J. N. Argyropoulis, Tetrahedron Lett.,23, 2273 (1982).
Sung-Kee Chung, J. Chem. Soc., Chem. Commun., No. 9, 480 (1982).
T. A. Geissman in: Organic Reactions, Vol. 2, John Wiley, New York (1944), p. 112.
Author information
Authors and Affiliations
Additional information
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 7, pp. 1567–1572, July, 1984.
Rights and permissions
About this article
Cite this article
Grinfel'ds, A.A., Artamkina, G.A. & Beletskaya, I.P. Oxidation of alcohols and aldehydes in KOH-dimethoxyethane-O2 systems. Russ Chem Bull 33, 1438–1442 (1984). https://doi.org/10.1007/BF00956521
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00956521