Ammonia → 2,3-Dichloro-4,6-dinitrophenol

Participants

Reaction Conditions

Reaction Steps

A 100 mL round-bottomed flask with stir bar is charged with 10 milliliters (mL) of liquid ammonia and 5.6 grams (g) (0.050 mol) of potassium t-butoxide. The resulting mixture is refluxed at -33° C. under a dry ice/acetone condenser and a nitrogen atmosphere. A solution of 2.4 g (0.010 mol) 1,2-dichloro-3,5-dinitrobenzene and 1.1 g (1.1 eq.) of 90% t-butyl hydroperoxide in 30 mL of N-methylpyrrolidinone is added dropwise over approximately 1 hour to the agitated refluxing liquid ammonia reaction mixture. Upon completion of the addition, the dry ice/acetone condenser is removed and the ammonia is allowed to evaporate under a stream of dry nitrogen. The crude 2,3-dichloro-4,6-dinitrophenol is isolated by pouring the reaction mixture into 50 mL of aqueous hydrochloric acid, extracted with ethyl acetate and the organic solvents evaporated under reduced pressure (15 mm). The yield of the product is 2.2 g (89%). This product is of sufficient purity to be used without further refinement.

Provenance & Evidence