1,2,4-Trichlorobenzene → 2,4,5-Trichloronitrobenzene

HRID 67808

Reaction equation

HRID 67808 reaction equation
OS(O)(=O)=O.[N+:6]([O-:9])(O)=[O:7].[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=1[Cl:18]>O>[Cl:10][C:11]1[CH:16]=[C:15]([N+:6]([O-:9])=[O:7])[C:14]([Cl:17])=[CH:13][C:12]=1[Cl:18]

Participants

5

Reactant 3

HCID 131,2,4-TrichlorobenzeneHCID 944Nitric AcidHCID 1118Sulfuric Acid

Product 1

HCID 69832,4,5-Trichloronitrobenzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 300 ml concentrated H2SO4 (98%) and 150 ml concentrated HNO3 (90%) was prepared in a 2 liter flask equipped with an agitator, thermometer, and dropping funnel. A total of 90.8 gm of 1,2,4-trichlorobenzene (0.5 mol) was added to the acid mixture at 70°-90° C. over a 1 hour period of time. The reaction was maintained at this temperature for 2 to 3 hours or until analysis of the reaction mixture showed the reaction to be complete. Work-up of the product involved addition of 1 liter of cold water to the reaction mass while maintaining a temperature from 55°-65° C. Separation of the organic and aqueous layers gave the desired product, 1,2,4-trichloro-5-nitrobenzene. Crude yield is 95-98% of theory with an isomer purity of 91-95%. Subsequent reactions outlined in Example 1 show this material to be suitable for preparation of TCDD free 2,4,5-TCP and 2,4,5-T.

Workup

  1. customwas prepared in a 2 liter flask
  2. customequipped with an agitator
  3. temperatureThe reaction was maintained at this temperature for 2 to 3 hours or until analysis of the reaction mixture
  4. customthe reaction
  5. temperaturewhile maintaining a temperature from 55°-65° C
  6. customSeparation of the organic and aqueous layers

Sources & evidence

ORD record
ord-dbb47070135340919bd1e9bb34f4eb9a
Source dataset
uspto-grants-1982_08
Patent number
US04346248

Linked notes

Loading…