Nitric Acid → 4-Methyl-3-nitrobenzonitrile

HRID 1282074Notes

Reaction equation

HRID 1282074 reaction equation
[C:1]1([CH3:9])[CH:6]=[CH:5][C:4]([C:7]#[N:8])=[CH:3][CH:2]=1.[N+:10]([O-])([OH:12])=[O:11]>S(=O)(=O)(O)O>[CH3:9][C:1]1[CH:6]=[CH:5][C:4]([C:7]#[N:8])=[CH:3][C:2]=1[N+:10]([O-:12])=[O:11]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 7724p-Tolunitrile

Product 1

HCID 5893334-Methyl-3-nitrobenzonitrile

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To conc. sulfuric acid (50 ml) was added p-tolunitrile (50 g) under ice-cooling and fuming nitric acid (38 ml) was added at the same temperature over 1 hr. The reaction mixture was poured into ice water (700 g) and the precipitated crystals were collected by filtration. The obtained crystals were washed with water to give yellow white crystals (90 g). The yellow white crystals were recrystallized from ethanol:water (9:1) to give the title compound (61 g) as white crystals.

Workup

  1. temperaturecooling
  2. filtrationthe precipitated crystals were collected by filtration
  3. washThe obtained crystals were washed with water

Sources & evidence

ORD record
ord-f1eb4883a14d4bd2bafeea87ee8db930
Source dataset
uspto-grants-2002_09
Patent number
US06455528B1

Reaction notes

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