Skip to main content
Log in

Anodic oxidation of p-methoxytoluene in acetic acid on graphite

  • Published:
Journal of Applied Electrochemistry Aims and scope Submit manuscript

Abstract

The direct oxidation of p-methoxytoluene in acetic acid medium was studied on a graphite anode for the preparation of p-anisaldehyde and p-anisyl acetate. The effect of the water contents of the solvent on the reaction selectivity was determined for solvent mixtures containing from 0 to 20 vol % water. In anhydrous medium p-anisyl acetate was the main product. When the water contents increased the yield of p-anisaldehyde increased. It was shown that the higher the proportion of water, the lower the p-methoxytoluene oxidation rate. The formation of products of consecutive oxidation steps decreased as the temperature increased from 60 to 90 °C.

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

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. S. Torii, ‘Electroorganic Syntheses-Methods and applications. Part I: Oxidations’, Kodansha, Ltd, Tokyo (1985).

    Google Scholar 

  2. S. Torii, Y. Wake and T. Okamoto, Japanese Patent Kokai, 52-125 137 (1977).

  3. BASF, Ger. Offen. 2 848 397 (1980); 2 851 732 (1980); 2 912 058 (1980).

  4. BASF, Ger. Offen. 2 935 398 (1981).

  5. H. Wendt and S. Bitterlich, Electrochim. Acta 37 (1992) 1951–8.

    Google Scholar 

  6. H. Wendt, S. Bitterlich, E. Lodowicks and Z. Liu, Electrochim. Acta 37 (1992) 1959–69.

    Google Scholar 

  7. H. J. Kim, K. Kusakabe, S. Hokazono, S. Morooka and Y. Kato, J. Appl. Electrochem. 17 (1987) 1213–22.

    Google Scholar 

  8. D. Degner, ‘Organic Electrosyntheses in Industry’, Topics in Current Chemistry, Springer-Verlag, 170 (1994) 113–229.

    Google Scholar 

  9. T. Tzédakis and A. Savall, Chem. Eng. Sci. 46 (1991) 2269–79.

    Google Scholar 

  10. Idem, Ind. Eng. Chem. Res. 31 (1992) 2475–83.

    Google Scholar 

  11. Idem, J. Appl. Electrochem. 27 (1997) 589–97.

    Google Scholar 

  12. G. Falgayrac and A. Savall, Catal. Today 24 (1995) 189–94.

    Google Scholar 

  13. G. Falgayrac, ‘Amélioration de l’ActivitéCatalytique de Métaux de Transition par Voie Electrochimique; Application à l’Oxydation de Toluènes en Phase Liquide par l’Oxygène Moléculaire Catalysée par le Cobalt’, Doctorat de l’UniversitéPaul Sabatier, Toulouse, France (1996).

    Google Scholar 

  14. G. Falgayrac, J. Serp and A. Savall, submitted.

  15. E. I. Heiba, R. M. Dessau and W. J. Koehl, J. Am. Chem. Soc. 91 (1969) 6830–7.

    Google Scholar 

  16. E. A. Mayeda, L. L. Miller and J. F. Wolf, J. Am. Chem. Soc. 20 (1972) 6812–6.

    Google Scholar 

  17. L. Eberson and K. Nyberg, Accounts Chem. Res. 6 (1973) 106–12.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Falgayrac, G., Savall, A. Anodic oxidation of p-methoxytoluene in acetic acid on graphite. Journal of Applied Electrochemistry 28, 1137–1140 (1998). https://doi.org/10.1023/A:1003409125132

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1003409125132

Navigation