Desulfonation reaction

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

RC6H4SO3H + H2O → RC6H5 + H2SO4
See also: Aromatic sulfonation

The reaction applied to aryl and naphthylsulfonic acids. It is the reverse of sulfonation.[1] The temperature of desulfonation correlates with the ease of the sulfonation. Desulfonation also applies to aromatic compounds.

Applications in synthesis

This reactivity is exploited in the regiospecific preparation of many di- and tri-substituted aromatic compounds. 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[2] and 2-bromophenol via phenol-2,4-disulfonic acid.[3]

References
  1. 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
  2. Harry P. Schultz (1951). "2,6-Dintroaniline". Org. Synth. 31: 45. doi:10.15227/orgsyn.031.0045.
  3. Ralph C. Huston, Murel M. Ballard (1934). "o-Bromophenol". Org. Synth. 14: 14. doi:10.15227/orgsyn.014.0014.{{cite journal}}: CS1 maint: uses authors parameter (link)
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