Sulfuric Acid → HCID 86737989, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of concentrated sulfuric acid (4.25 g) and water (17.3 g) is cooled to about 12° C., and a solution of {5-[(1-ethylpropyl)amino]-4,6-dinitro-o-cumenyl}acetaldehyde (6.5 g; 0.0192 mol) in methylene chloride (40 ml) is added slowly while the temperature of the mixture is maintained at about 12° C. Next, potassium permanganate (3.0 g; 0.0192 mol) is added to small portions. After stirring overnight at room temperature, tlc indicates the presence of some starting material. The mixture is cooled to 15° C., and a second portion of potassium permanganate (3.0 g; 0.0192 mol) added. When tlc indicates the absence of starting material, sodium thiosulfate is added until a clear red solution is obtained. Methylene chloride is added and the layers are separated. The methylene chloride layer is washed, dried over magnesium sulfate, and evaporated to leave a red oil (6.6 g; 97%) which slowly solidifies to a yellow solid. This solid is purified by column chromatography using 90/10 toluene/ethyl acetate to elute the product, melting point 116°-118° C. An analytical sample, recrystallized from pentane, melts at 117.5°-118.5° C.

Provenance & Evidence