Nitric Acid → 2,6-Dichloro-3-nitrotoluene

HRID 2396936Notes

Reaction equation

HRID 2396936 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH3:9].[N+:10]([O-])([OH:12])=[O:11]>>[Cl:1][C:2]1[C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH3:9]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 83682,6-Dichlorotoluene

Product 1

HCID 971552,6-Dichloro-3-nitrotoluene

Procedure

To 2,6-dichlorotoluene (200 g) is added dropwise fuming nitric acid (d=1.52, 206 ml) at 25° to 30° C. After stirring for 30 minutes at room temperature, the mixture is poured into ice-water, extracted with diethyl ether, and the extract is washed with an aqueous sodium hydrogen carbonate solution and then dried. The solvent is distilled off under reduced pressure to give 2,6-dichloro-3-nitrotoluene as yellow crystals (253.2 g).

Workup

  1. extractionextracted with diethyl ether
  2. washthe extract is washed with an aqueous sodium hydrogen carbonate solution
  3. customdried
  4. distillationThe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-e34ba42880904706a31517e802053ca5
Source dataset
uspto-grants-1996_02
Patent number
US05495020

Reaction notes

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