Desulfonation reaction

In organic chemistry, the desulfonation reaction is the hydrolysis of sulfonic acids. The reaction mainly applied to aryl and naphthylsulfonic acids. It is the reverse of sulfonation.[1] The temperature of desulfonation correlates with the ease of the sulfonation:

RC6H4SO3H + H2O → RC6H5 + H2SO4

This reactivity is exploited in the regiospecific preparation of 2-chlorotoluene by chlorination of p-toluenesulfonic acid, followed by hydrolysis of the intermediate. The method is also useful for the preparation of 2,6-dinitroaniline.[2]

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.
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