Sulfuric Acid → 5-Nitrobenzene-1,2,3-tricarboxylic acid

Reaction equation

[C:1]1([C:13]([OH:15])=[O:14])[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([OH:9])=[O:8])[C:2]=1[C:10]([OH:12])=[O:11].S(=O)(=O)(O)O.[N+:21]([O-])([O-:23])=[O:22].[K+]>O>[N+:21]([C:5]1[CH:6]=[C:1]([C:13]([OH:15])=[O:14])[C:2]([C:10]([OH:12])=[O:11])=[C:3]([C:7]([OH:9])=[O:8])[CH:4]=1)([O-:23])=[O:22]

Participants

Procedure

To a stirred mixture of 125 g. of 1,2,3-benzenetricarboxylic acid and 900 ml. of concentrated sulfuric acid at 60°-70° C. is added, gradually over a 2 hour period, 312 g. of potassium nitrate. The mixture is heated at 135°-140° C. for 16 hours, cooled and treated with ice and water. Some solid is seprated out and is dissolved in water. The entire aqueous mixture is extracted with ether, the extract is washed with water and dried over magnesium sulfate. The ether is concentrated to a small volume, and petroleum ether is added to precipitate a white solid. The solid is collected and dried to give 76.5 g. of the product of the Example.