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Solid sodium nitrite in anhydrous propionic acid is an effective system for regioselective nitrosation of the subject compounds. High yields of pure 2-nitroso products are obtained rapidly and efficiently. Attack at the 4-position becomes competitive if water is present in the medium. The 5-alkoxy (but not the 3,5-dialkoxy)-2-nitrosphenols can be easily oxidized with nitric acid to yield the corresponding 2-nitro compounds.
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