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Catalytic transformations of 1-furyl-2-oxa-4-butanol

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Conclusions

  1. 1.

    The hydrogenation of 1-furyl-2-oxa-4-butanol in a flow system at normal pressure on a Pd-C-catalyst at 180° and 280°, and also on Raney Cu-Al- and Ni-Al-catalysts at 240° were studied.

  2. 2.

    At 180° on a Pd-C-catalyst, 1-furyl-2-oxa-4-butanol smoothly hydrogenates to 1-tetrahydrofuryl-2-oxa-4-butanol. Raising the temperature to 280° makes possible the hydrogenolysis of the ether bond in the side chain.

  3. 3.

    The Cu-Al-catalyst possesses the property of most effectively causing hydrogenolysis of the side ether bond (50%), whereas hydrogenolysis of the furan ring with subsequent cyclodehydration leading to propyldioxane is observed to a lesser degree (20%).

  4. 4.

    “Conjugated” hydrogenolysis of the furan ring occurs on the Raney Ni-Al-catalyst leading to the formation of methyl-, ethyl-, and propyldioxanes from 1-furyl-2-oxa-4-butanol in yields of 18, 10, and 14%, respectively.

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Literature cited

  1. 1.

    N. I. Shuikin, I. F. Bel'skii, and Kh. M. Minachaev, Zh. obshch, khimii,29, 2969 (1959).

  2. 2.

    N. I. Shuikin, V. I. Nikiforov, and P. A. Stolyarova, Zh. obshch. khimii,7, 1501 (1937).

  3. 3.

    N. I. Shuikin and I. F. Bel'skii, Dokl. AN SSSR,115, 330 (1957).

  4. 4.

    N. I. Shuikin and I. F. Bel'skii, Dokl. AN SSSR,125, 345 (1959).

  5. 5.

    N. I. Shuikin and I. F. Bel'skii, Izv. AN SSSR, Otd. khim. n.,1958, 309.

  6. 6.

    N. I. Shuikin and I. F. Bel'skii, Zh. obshch. khim.,29, 3627 (1959).

  7. 7.

    I. F. Bel'skii, Izv. AN SSSR, Otd. khim. n.,1962, 142.

  8. 8.

    I. F. Bel'skii, N. I. Shuikin, and G. E. Skobtsova, Izv. AN SSSR, Otd. khim. n.,1963, 9.

  9. 9.

    I. F. Bel'skii, N. I. Shuikin, and V. M. Shostakovskii, Dokl. AN SSSR,152, 862 (1963).

  10. 10.

    I. F. Bel'skii, S. N. Khar'kov, and N. I. Shuikin, Dokl. AN SSSR,165, 821 (1965).

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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 2109–2111, September, 1967.

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Shuikin, N.I., Bel'skii, I.F. & Khar'kov, S.N. Catalytic transformations of 1-furyl-2-oxa-4-butanol. Russ Chem Bull 16, 2034–2036 (1967). https://doi.org/10.1007/BF00909615

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Keywords

  • Hydrogenation
  • Methyl
  • Ether
  • Ethyl
  • Furan