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Products of reaction between tetrabromo-substituted ortho- and para-hydroxybenzoic acids and sodium nitrite in CH3COOH

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Abstract

The reaction of 2,3,5,6-tetrabromo-4-hydroxybenzoic acid with a 10-fold excess of NaNO2 in the glacial acetic acid at 20°C affords tetrabromonitrosophenols whose further transformations under the reaction conditions leads to the formation of a mixture of 2,4,5,6-tetrabromo-p-quinone diazide and tetrabromo-p- and -o-nitrophenols in the molar ratio 37: 2: 1. Under similar conditions the 3,4,5,6-tetrabromo-2-hydroxybenzoic acid is converted into a mixture of 3,4,5,6-tetrabromo-o-quinone diazide with the same nitrophenols in the ratio 13: 1: 3. The reaction of sodium 2,3,5,6-tetrabromo-4-hydroxy-benzoate with NaNO2 in dilute acetic acid resulted in a quantitative yield of tetrabromo-p-quinone monooxime.

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Authors and Affiliations

  1. Ogarev Mordovian State University, Saransk, 430005, Russia

    M. V. Fadin, I. V. Tarasova, V. A. Vasin & V. N. Shishkin

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  1. M. V. Fadin
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  2. I. V. Tarasova
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  3. V. A. Vasin
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  4. V. N. Shishkin
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Correspondence to M. V. Fadin.

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Original Russian Text © M.V. Fadin, I.V. Tarasova, V.A. Vasin, V.N. Shishkin, 2012, published in Zhurnal Organicheskoi Khimii, 2012, Vol. 48, No. 8, pp. 1066–1074.

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Fadin, M.V., Tarasova, I.V., Vasin, V.A. et al. Products of reaction between tetrabromo-substituted ortho- and para-hydroxybenzoic acids and sodium nitrite in CH3COOH. Russ J Org Chem 48, 1062–1070 (2012). https://doi.org/10.1134/S1070428012080064

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  • DOI: https://doi.org/10.1134/S1070428012080064

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