Summary
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1.
The Rodionov-Matveev reaction was extended to p-hydroxybenzoic acid and 1-phenol-4-sulfonic acid, and diazo compounds were obtained in yields of 75–90%.
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2.
When the Sandmeyer reaction was carried out on the diazo solution obtained from p-hydroxybenzoic acid, 3-chlora-4-hydroxybenzoic acid and 4-chloro-2-nitrophenol were formed. This indicates that the primary reaction products were 5-carboxy-2-hydroxybenzenediazonium and 4-hydroxy-3-nitrobenzenediazonium salts.
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Literature cited
V. M. Rodionov and V. K. Matveev, Berichte 57, 1711 (1924).
L. G. Makarova and A. N. Nesmeianov, J. Gen. Chem. 9, 771 (1939); A. N. Nesmeianov and S. T. Ioffe, J. Gen. Chem. 11, 392 (1941). [USSR]
A. A. Nemodruk, Dissertation, Moscow, 1952.
S. Kostanecki, see, G. Heller, Berichte 45, 675 (1912)
A. Faust and E. Saame, Ann. Suppl. 7, 191 (1870).
K. Auwers, Berichte 30, 1474 (1897).
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The term “diazotization” is used in the Russian text with an explanatory footnote; we consider that the term “diazoation” is more appropriate for the reaction under discussion. — Publisher.
This work was carried out under the direction and with the participation of Academician V. M. Rodionov.
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Belikov, V.M. “Diazoation” of p-hydroxybenzoic and 1-phenol-4-sulfonic acids. Russ Chem Bull 7, 1431–1433 (1958). https://doi.org/10.1007/BF00914858
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DOI: https://doi.org/10.1007/BF00914858