[N:1]([O-:3])=[O:2].[Na+].[CH3:5][O:6][C:7]1[CH:8]=[C:9]([OH:13])[CH:10]=[CH:11][CH:12]=1>O.C(O)(=O)CC>[CH3:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N:1]=[O:3])=[C:9]([OH:13])[CH:8]=1.[CH3:5][O:6][C:7]1[CH:8]=[C:9]([OH:13])[CH:10]=[CH:11][C:12]=1[N:1]=[O:2]A solution of sodium nitrite (6.9 g, 0.1 mol) dissolved in 15 mL water was added, dropwise, to a solution of 3-methoxyphenol (12.4 g, 0.1 mol) dissolved in propionic acid (100 mL) cooled to -5° to 0° C., at a rate which maintained a temperature of -5° to 0° C. The mixture was stirred for 1 hour to produce a slurry of alkoxy nitrosophenols having a mole ratio of 5-methoxy-2-nitrosophenol to 3-methoxy-4-nitrosophenol of 95:5. Water (85 mL) was added to the slurry and the product was collected by filtration, washed with 60 mL of 50% aqueous propionic acid and then dried to give 10.1 g (66% of theory) of 5-methoxy-2-nitrosophenol which contained approximately 2% of the 3-methoxy-4-nitrosophenol isomer.
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