Chemistry:Conversion of diazonium salt to phenol

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The thermal decomposition of aryl diazonium salts in aqueous solutions occurs over the time and can be accelerated upon heating.[1] This can occur as an unwanted side reaction leaving phenol as side product(s);[2] or be utilized as a shortcut in Organic Chemistry, for the synthesis of phenols.[3]

Reaction Summary

Primary aryl amines react with Sodium nitrite in acid solution and let to boil. [3] This converts the produced diazonium salt to phenol. To sum up, a convenient conversion of amine to phenol via diazotization.

Übersichtsreaktion der Phenolverkochung.svg

Mechanism 

This thermal decomposition starts with the elimination diazonium group in the form of nitrogen gas that leaves the aromatic moiety as a cation, that is extremely reactive. The produced aryl cation reacts with water and yields the corresponding phenol. Therefore, arylamines can be simply converted to phenols via diazotization and boiling their solution.[3] This has been utilized for the preparation dihydroxyl carrying analogues of the Tröger’s base. [3]


References 

  1. Carey, F. A.; Sundberg, R. J. (2007). Advanced Organic Chemistry. Vol. B, Chapter 11: Springer. pp. 1028. 
  2. Khazaei, A.; et. al., (2013). "Diazonium to phenol". J. Appl. Polym. Sci. 129: 3439. https://doi.org/10.1002/app.39069. 
  3. 3.0 3.1 3.2 3.3 "Facile Preparation of Phenol". Synlett 28: 1641. 2017. http://dx.doi.org/10.1055/s-0036-1588180.