Catalytic hydrogenation of (+)-p-mentha-6, 8-dien-2-one over a nickel catalyst

  • L. F. Godunova
  • E. I. Klabunovskii
  • A. A. Balandin
  • E. A. Oger
  • I. A. Rubtsov
Organic and Biological Chemistry

Conclusions

  1. 1.

    A study was made of the sequence and stereochemistry of processes in the hydrogenation of (+)-p-mentha-6,8-dien-2-one over Raney nickel in ethanol at 20°.

     
  2. 2.

    Procedure for the Chromatographic analysis of the reaction products was worked out.

     
  3. 3.

    The hydrogenation of p-mentha-6,8-dien-2-one goes through the intermediate formation of p-menth-8-en-2-one, iso-p-menth-8-en-2-one, and p-menth-6-en-2-one, which are then hydrogenated to isomeric p-menthan-2-ones, and these further to four isomeric p-menthan-2-ols.

     
  4. 4.

    The pH of the medium affects not only the rate of the process, but also the selectivity and the course of the process; in an alkaline medium the hydrogenation of p-mentha-6,8-dien-2-one goes selectively through the formation of intermediate p-menth-8-en-2-one and iso-p-menth-8-en-2-one.

     

Keywords

Hydrogenation Nickel Chromatographic Analysis Alkaline Medium Intermediate Formation 

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Literature cited

  1. 1.
    S. Mitsui, J. Soc. Org. Syn. Japan,17 (11), 640 (1959).Google Scholar
  2. 2.
    R. Berell, In: New Methods for the Study of Heterogeneous Catalysis [Russian translation], IL (1963), p. 38.Google Scholar
  3. 3.
    S. Siegel, Advances in Catalysis,16, 123 (1966).Google Scholar
  4. 4.
    E. F. Armstrong and T. P. Hilditch, Proc. Roy. Soc.,108A, 128 (1925).Google Scholar
  5. 5.
    H. Rupe, Liebigs Ann.,45A, 195 (1927).Google Scholar
  6. 6.
    A. Haller and C. Martine, Compt. rend.,140, 1302 (1905).Google Scholar
  7. 7.
    W. N. Ipatief and G. Balchinsky, Ber.,44, 3461 (1911).Google Scholar
  8. 8.
    M. Badocne, Bull. Soc. chim. France,4, 21 (1937).Google Scholar
  9. 9.
    A. A. Pavlis, J. Am. Chem. Soc.,68, 1471 (1946).Google Scholar
  10. 10.
    L. F. Godunova, E. I. Klabunovskii, and A. A. Balandin, Izv. Akad. Nauk SSSR, Ser. Khim,1967, 1013.Google Scholar
  11. 11.
    S. Mitsui and S. Imaizumi, J. Chem. Soc. Japan,86, 219 (1965).Google Scholar
  12. 12.
    A. M. Sokol'skaya, S. M. Reshetnikov, and K. K. Kuzenbaev, Trudy Inst. Khim. Nauk Akad. Nauk KazakhSSR,14, 57 (1966).Google Scholar
  13. 13.
    L. V. Sokol'skii, Hydrogenation in Solution [in Russian], Izd. AN KazakhSSR, Alma-Ata (1962), p. 425.Google Scholar
  14. 14.
    J. Read and R. G. Johnston, J. Chem. Soc.,1934, 226.Google Scholar

Copyright information

© Consultants Bureau 1969

Authors and Affiliations

  • L. F. Godunova
    • 1
  • E. I. Klabunovskii
    • 1
  • A. A. Balandin
    • 1
  • E. A. Oger
    • 1
  • I. A. Rubtsov
    • 1
  1. 1.N. D. Zelinskii Institute of Organic ChemistryAcademy of Sciences of the USSRUSSR

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