Rj. Maleski et al., A FACILE ACCESS TO SUBSTITUTED 2-NITROSOPHENOLS AND 2-NITROPHENOLS VIA REGIOSELECTIVE NITROSATION OF RESORCINOL MONOETHERS, Synthetic communications, 25(15), 1995, pp. 2327-2335
Solid sodium nitrite in anhydrous propionic acid is an effective syste
m for regioselective nitrosation of the subject compounds. High yields
of pure 2-nitroso products are obtained rapidly and efficiently. Atta
ck at the 4-position becomes competitive if water is present in the me
dium. The 5-alkoxy (but not the 3,5-dialkoxy)-2-nitrosphenols can be e
asily oxidized with nitric acid to yield the corresponding 2-nitro com
pounds.