Summary
Hydrolysis of 2-(β -cyclohexylideneethyl)dihydroresorcinol (II) gives an unsaturated keto acid (VIII) which is converted by a double cyclization under the influence of polyphosphoric acid to 1-keto-Δ9,11,13 -octahydrophenanthrene (XV). This series of reactions can be useful for the synthesis of polycyclic compounds related to steroids.
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V. I. Gunar, S. I. Zav'yalov, and A. I. Krotov, Izvest. Akad. Nauk SSSR, Otdel. Khim. Nauk, 535 (1959).
S. I. Zav'yalov, V. I. Gunar, G. N. Pershin, and S. N. Milovanova, Izvest. Akad. Nauk SSSR, Otdel. Khim. Nauk 1241 (1960).
I. N. Nazarov, S. N. Anachenko, and I. V. Torgov, Zhur. Obshch. Khim.26, 819 (1956).
I. N. Nazarov, G. P. Verkholetova, S. N. Anachenko, I. V. Torgov, and G. V. Aleksandrova, Zhur. Obshch. Khim.26, 1482 (1956).
L. Fieser, J. Amer. Chem. Soc.51, 2462 (1929).
A. Pschorr, Ber.39, 3111 (1906).
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Zav'yalov, S.I., Gunar, V.I. & Kudryavtseva, L.F. Chemistry of dihydroresorcinol. Russ Chem Bull 9, 1865–1868 (1960). https://doi.org/10.1007/BF00907747
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DOI: https://doi.org/10.1007/BF00907747