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

HRID 1609377Notes

Reaction equation

N.CC(C)([O-:5])C.[K+].[Cl:8][C:9]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[C:11]([N+:18]([O-:20])=[O:19])[C:10]=1[Cl:21].C(OO)(C)(C)C>CN1CCCC1=O>[Cl:8][C:9]1[C:10]([Cl:21])=[C:11]([N+:18]([O-:20])=[O:19])[CH:12]=[C:13]([N+:15]([O-:17])=[O:16])[C:14]=1[OH:5]

Participants

Conditions

Temperature: -33 °C

Procedure

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.

Workup

temperaturerefluxing
additionUpon completion of the addition
customthe dry ice/acetone condenser is removed
customto evaporate under a stream of dry nitrogen

Sources & evidence

ORD record: ord-a6edbf2b3a35445086a849b4995ee3d9
Source dataset: uspto-grants-1995_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05399768

Reaction notes

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