3-Methoxyphenol → 5-Methoxy-2-nitrosophenol

Participants

Reaction Steps

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.

Provenance & Evidence