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Cycloalkenylation of phenol with 1,3-cyclohexadiene

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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Summary

  1. 1.

    The cycloalkenylation of phenol with 1,3-cyclohexadiene in the presence of a mixture of phosphoric and sulfuric acids was studied.

  2. 2.

    The reaction products were o-(cyclohexen-2-yl)phenol in 39% yield and p-(cyclohexen-2-yl)phenol in 28% of theoretical yield.

  3. 3.

    Isomerization of o- and p-(cyclohexen-2-yl)phenols in the presence of potassium hydroxide gave the corresponding (cyclohexen-1-yl)phenols.

  4. 4.

    The cyclization product of o-(cyclohexen-2-yl)phenol was 2,3-cyclohexano-2,3-dihydrobenzofuran.

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Literature cited

  1. A. Bader, J. Amer. Chem. Soc.75, 5967 (1953).

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  2. E. A. Viktorova, N. I. Shuikin, and P. N. Komarov, Vestnik MGU (in press).

  3. E. A. Viktorova, N. I. Shuikin, and G. S. Korosteleva, Vestnik MGU (in press).

  4. N. A. Domnin and A. S. Beletskaya, Zhur. Obshchei Khim.,24, 1636 (1954).

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  5. I. Heilbron and H. M. Bunbury, Dictionary of Organic Compounds [Russian translation] (IL, Moscow, 1949), pp. 598–599.

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Authors and Affiliations

  1. M. V. Lomonosov Moscow State University, USSR

    E. A. Viktorova, N. I. Shuikin & E. I. Polnyanskya

Authors
  1. E. A. Viktorova
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  2. N. I. Shuikin
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  3. E. I. Polnyanskya
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Viktorova, E.A., Shuikin, N.I. & Polnyanskya, E.I. Cycloalkenylation of phenol with 1,3-cyclohexadiene. Russ Chem Bull 9, 1899–1900 (1960). https://doi.org/10.1007/BF00907756

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  • DOI: https://doi.org/10.1007/BF00907756

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