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Electrochemical reactions of halohydrins. I. Attempt at reductive coupling

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Abstract

The electrochemical reductive coupling of 2-chloroethanol and 2-bromoethanol to 1,4-butanediol was attempted. The electrochemical cleavage of the carbon-halogen bond leads to intermediates which are either unstable and decompose to ethylene and OH−, or undergo chemical reactions leading to ether formation. The presence of the hydroxyl group in halohydrins seems to be responsible for the observed reaction paths. When the alcohol group was protected by esterification, coupled products were observed. Coupling of bromoethyl acetate to 1,4-butanediol diacetate thus appears technically feasible, but is a commercially less attractive route to 1,4-butanediol.

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References

  1. US Patent no. 577 277 (1946).

  2. German Patent no. 2 008 568 (1970).

  3. German Patent no. 2 015 282 (1970).

  4. German Patent no. 2 131 177 (1971).

  5. L. Eberson and H. Schaefer, “Topicis in Current Chemistry’, Vol. 21, Springer-Verlag, New York (1971).

    Google Scholar 

  6. M. R. Rifi, ‘Org. Electrochem’, Ch. VI (ed. M. M. Baizer) Marcel Dekker, New York (1973).

    Google Scholar 

  7. J. Casanova and I. Eberson. ‘The Chemistry of Carbon-Halogen Bond’, Part 2, Ch. 15 (ed. S. Patai) Wiley, New York (1973).

    Google Scholar 

  8. M. M. Baizer, ‘Org. Electrochem.’, Ch. XIX, (ed. M. M. Baizer) Marcel Dekker, New York (1973) p. 684.

    Google Scholar 

  9. A. P. Tomilov, S. G. Mairanovskii, M. Ya. Fioshin and V. A. Smirnov, ‘Electrochemistry of Organic Compounds’, Khimya, Leningrad (1968).

    Google Scholar 

  10. L. G. Feoktistov and S. I. Zhdanov,Electrochem. Acta 10 (1965) 657.

    Google Scholar 

  11. L. G. Feokstov, A. P. Tomilov, Yu. D. Smirnov and M. M. Goldin,Sov. Electrochem. 1 (1965) 791.

    Google Scholar 

  12. D. J. Barclay,J. Electroanalyt. Chem. 28 (1970) 493.

    Google Scholar 

  13. R. R. Adzic and A. R. Despic,J. Chem. Phys. 64 (1974) 3482.

    Google Scholar 

  14. R. R. Adzic, D. N. Simic, D. M. Drazic and A. R. Despic,J. Electroanalyt. Chem. 61 (1975) 117.

    Google Scholar 

  15. Idem, ibid 80 (1977) 81.

    Google Scholar 

Download references

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Authors and Affiliations

  1. Corporate Research Center, Allied Chemical Corporation, PO Box 1021R, 07960, Morristown, New Jersey, USA

    D. Cipris

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  1. D. Cipris
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Cipris, D. Electrochemical reactions of halohydrins. I. Attempt at reductive coupling. J Appl Electrochem 8, 537–544 (1978). https://doi.org/10.1007/BF00610799

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  • DOI: https://doi.org/10.1007/BF00610799

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