N-Methyl-N-nitrosourea → 4-Nitroanisole

Participants

Reaction Conditions

Reaction Steps

0.80 grams (5 millimoles) of anhydrous sodium p-nitrophenolate and 0.52 grams (5 millimoles) of N-methyl,N-nitrosourea were added to 25 milliliters of 1,2-dimethoxyethane kept dry with molecular sieves and a drying tube. This mixture was maintained at 0° C. for one hour and then elevated to room temperature for six hours while constant stirring was maintained. Solvent was evaporated and the residue treated simultaneously with ether and water. This mixture was shaken and the aqueous layer was removed. The ether layer was washed with potassium hydroxide (0.1 N, 3× 50 milliliters) to remove any unreacted phenol. The ether layer was washed with water (3×50 milliliters) and dried with magnesium sulfate. Filtration afforded a clear solution which was concentrated under diminished pressure to yield 0.70 grams of p-nitroanisole (about 90 percent, melting point 52°-53°. This was shown to be identical with an authentic sample.

Provenance & Evidence