Nitric Acid → 2-Nitrotoluene

HRID 1071874Notes

Reaction equation

HRID 1071874 reaction equation
[C:1]1([CH3:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+:8]([O-])([OH:10])=[O:9]>>[N+:8]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[CH3:7])([O-:10])=[O:9]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 1140Toluene

Product 1

HCID 69442-Nitrotoluene

Procedure

Toluene (0.91 g, 10 mmol), 68% nitric acid (30% mmol, 2.8 g) and [C4min][OTf] (0.57 g, 2 mmol) and heated (oil bath at 110° C.) in a 25 ml round bottom flask equipped with a reflux condenser for 24 hours. The reaction mixture is cooled to room temperature and the nitrotoluene/residual nitric acid is distilled off at 140° C. at 1 mBar. Phase separation of the distillate yields pure nitrotoluene as a mixture of 2- and 4-isomers. The ionic liquid remains in the distillation flask and can be reused on further reactions.

Workup

  1. customequipped with a reflux condenser for 24 hours
  2. distillationthe nitrotoluene/residual nitric acid is distilled off at 140° C. at 1 mBar
  3. customPhase separation of the distillate

Sources & evidence

ORD record
ord-9fe73ad8150d4ab6a37f23e8cc63a319
Source dataset
uspto-grants-2005_06
Patent number
US06906231B2

Reaction notes

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