Phenol → 2,5-dimethyl-4-nitrosophenol

Participants

Reaction Steps

A solution of 20 mL of 36N sulfuric acid solution in 40 mL of water (60 mL of 12N sulfuric acid) is added to a mixture of 6I g (500 mmol) of 2,5-xylenol and 200 mL of glacial acetic acid. A homogeneous solution is produced initially, but on continued stirring some of the phenol crystallizes. A solution of 35 g (500 mmol) of sodium nitrite in 60 mL of water is added dropwise to the previous mixture over 60 minutes at 5° to 10° C. Stirring is continued for 10 to 15 minutes and the heterogeneous mixture is poured into 1 L of water. The reaction flask is rinsed with water and the solid nitroso derivative collected, washed with water, and dried to a moist cake.

Provenance & Evidence