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31.5.1.1.12.1 Variation 1: Thermal Hydrolysis

DOI: 10.1055/sos-SD-031-00236

González-Bello, C.; Castedo, L.Science of Synthesis, (200731294.

The thermal decomposition of arenediazonium salts in a highly acidic aqueous medium affords the corresponding phenols in good yields. The reaction proceeds via an aryl cation intermediate that is trapped by water.[‌106‌] High acidity is required in order to avoid ionization of the phenol product to the corresponding phenoxide, which readily couples with any unreacted diazonium salt to give the corresponding azo derivative.[‌107‌] Using this method, an aqueous solution of the diazonium salt 47, obtained by diazotization of aniline 46, gives the phenol 48 in 93% yield (Scheme 23).[‌108‌]

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