Nitric Acid → 2,3,4-Trichloronitrobenzene

HRID 636365Notes

Reaction equation

HRID 636365 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[Cl:9].[N+:10]([O-])([OH:12])=[O:11]>S(=O)(=O)(O)O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:10]([O-:12])=[O:11])=[C:4]([Cl:8])[C:3]=1[Cl:9]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 68951,2,3-Trichlorobenzene

Product 1

HCID 286972,3,4-Trichloronitrobenzene

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

A mixture of 9.0 kg of 1,2,3-trichlorobenzene in 13.32 L of concentrated sulfuric acid is acid by drops to a solution of 4.13 L of 70% nitric acid and 4.13 L of concentrated sulfuric acid at 25-30° C. The slurry is stirred for 1.5-2 hours, then poured over 35 kg of ice and filtered. The filter cake is washed (15 L water) and then dissolved in 58 L of ethyl acetate. The organic phase is washed with water, aqueous sodium bicarbonate solution, and aqueous sodium chloride solution. The solution is dried over magnesium sulfate and concentrated to give the title product.

Workup

  1. customat 25-30° C
  2. filtrationfiltered
  3. washThe filter cake is washed (15 L water)
  4. dissolutiondissolved in 58 L of ethyl acetate
  5. washThe organic phase is washed with water, aqueous sodium bicarbonate solution, and aqueous sodium chloride solution
  6. dry with materialThe solution is dried over magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2266022b3c2b4c089ee2e65a2844c88c
Source dataset
uspto-grants-2001_02
Patent number
US06194420B1

Reaction notes

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