In organic chemistry, the desulfonation reaction is the hydrolysis of sulfonic acids:[1]

RC6H4SO3H + H2O → RC6H5 + H2SO4

The reaction applied to aryl and naphthylsulfonic acids. It is the reverse of sulfonation.[2] The temperature of desulfonation correlates with the ease of the sulfonation.

Applications in synthesis

This reactivity is exploited in the regiospecific preparation of many di- and tri-substituted aromatic compounds. The approach exploits the meta-directing effect of the sulfonic acid group. 2-Chlorotoluene for example can be prepared by chlorination of p-toluenesulfonic acid, followed by hydrolysis. The method is also useful for the preparation of 2,6-dinitroaniline[3] and 2-bromophenol via phenol-2,4-disulfonic acid.[4]

References

  1. ^ Smith, Michael B.; March, Jerry (2007), Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (6th ed.), New York: Wiley-Interscience, p. 749, ISBN 978-0-471-72091-1
  2. ^ Otto Lindner, Lars Rodefeld "Benzenesulfonic Acids and Their Derivatives" in Ullmann's Encyclopedia of Industrial Chemistry 2005, Wiley-VCH, Weinheim. doi:10.1002/14356007.a03_507
  3. ^ Harry P. Schultz (1951). "2,6-Dintroaniline". Org. Synth. 31: 45. doi:10.15227/orgsyn.031.0045.
  4. ^ Ralph C. Huston; Murel M. Ballard (1934). "o-Bromophenol". Org. Synth. 14: 14. doi:10.15227/orgsyn.014.0014.
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