Springer Nature is making SARS-CoV-2 and COVID-19 research free. View research | View latest news | Sign up for updates

Zur Sauerstoffoxidation von Kreosolderivaten in alkalisch-wäßriger Lösung

Oxygenation of creosol derivates in aqueous alkaline solution

  • 34 Accesses

  • 5 Citations

Abstract

Creosol (1), bicreosol (4) and other monomeric and dimeric creosols are oxidized in 0.25M-NaOH (5 equivalents base per phenolic hydroxyl group) by molecular oxygen at 70°C. Creosol is fragmented under these conditions to low molecular weight products without previous dimerization. The importance of fragmentation processes without cleavage of the C−C-bond between the oxygen substituted ring atoms in the case of bicreosol, and its considerable stability against oxidation compared with other compounds investigated can be explained by the ability of the monoanion of4 to exist in a conformation allowing hydrogen bonding between the phenolic oxygens of the two rings.

This is a preview of subscription content, log in to check access.

Literatur

  1. 1

    Siehe z. B.H.-m. Chang, W. T. McKean, J. S. Gratzl undC. K. Lin, Tappi56, Nr. 9, 116 (1973);H.-m. Chang, J. S. Gratzl undW. T. McKean, Tappi57, Nr. 5, 123 (1974), und die dort zitierte Literatur.

  2. 2

    K. Kratzl, J. Gratzl undP. Claus, Adv. Chem. Series59, 157 (1966).

  3. 3

    K. Kratzl undF. W. Vierhapper, Mh. Chem.102, 224, 425 (1971).

  4. 4

    K. Kratzl, F. W. Vierhapper undE. Tengler, Mh. Chem.106, 321 (1975).

  5. 5

    K. Kratzl, P. Claus undF. W. Vierhapper, Mh. Chem.103, 100 (1972).

  6. 6

    K. Kratzl, P. Claus, F. W. Vierhapper undE. Tengler, Vortrag Fourth Canadian Wood Chemistry Symposium, Quebec, Canada, Juli 1973. Vortrag 166th National Meeting, ACS, Chicago, USA, August 1973.

  7. 7

    S. Sundin, M. R. SanClemente undK. V. Sarkanen, Vortrag 167th National Meeting, ACS, Los Angeles, März-April 1974.

  8. 8

    E. L. Eliel, Stereochemistry of Carbon Compounds. McGraw-Hill. 1962;K. Mislow, Einführung in die Stereochemie. Verlag Chemie. 1967.

  9. 9

    H. Musso undH.-G. Matthies, Chem. Ber.94, 356 (1961); s. auchW. F. Baltinger, Jr.,P. v. R. Schleyer undK. Mislow, J. Amer. Chem. Soc.87, 3168 (1965).

  10. 10

    C. W. Bailey undC. W. Dence, Tappi52, 491 (1969).

  11. 11

    K. Kratzl, P. Claus, W. Lonsky undJ. S. Gratzl, Wood Science and Technology8, 35 (1974).

  12. 12

    F. W. Vierhapper undE. Tengler, unveröffentlichte Beobachtungen. An der vergleichenden Oxidation von Carbonsäuren mit Guajacylstruktur wird gearbeitet.

  13. 13

    Überlegungen dieser Art aus Ergebnissen mit tert. Butylguajakolen:R. C. Eckert, H.-m. Chang undW. P. Tucker, Tappi56, Nr. 6, 134 (1973);J. Gierer undF. Imsgard, Vortrag 166th National Meeting, ACS, Chicago, USA, August 1973.

  14. 14

    R. Schwarz undH. Herling, Org. Synth., Coll. Vol. IV, 203.

  15. 15

    Huang-Minlon, J. Amer. Chem. Soc.68, 2487 (1946).

  16. 16

    Modifiziert nach der Darstellung von 4-Hydroxy-5-methoxy-isophthalaldehyd:E. Profft undW. Krause, Arch. Pharm.298, 148 (1965).

  17. 17

    R. H. F. Manske undA. E. Ledingham, Canad. J. Res.22 B, 115 (1944).

  18. 18

    J. Koetschet undP. Koetschet, Helv. Chim. Acta13, 474 (1930).

  19. 19

    J. M. Bruce undF. K. Sutchiffe, J. Chem. Soc. 3824 (1956).

  20. 20

    S. L. Cosgrove undW. A. Waters, J. Chem. Soc.1949, 3189.

Download references

Author information

Correspondence to Prof. Dr. Karl Kratzl.

Additional information

Mit 1 Abbildung

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Vierhapper, F.W., Tengler, E. & Kratzl, K. Zur Sauerstoffoxidation von Kreosolderivaten in alkalisch-wäßriger Lösung. Monatshefte für Chemie 106, 1191–1201 (1975). https://doi.org/10.1007/BF00906232

Download citation