Sulfuric Acid → 2,4-Dimethyl-3-nitrophenol

HRID 1154005Notes

Reaction equation

HRID 1154005 reaction equation
[CH3:1][C:2]1[C:8]([N+:9]([O-:11])=[O:10])=[C:7]([CH3:12])[CH:6]=[CH:5][C:3]=1N.[OH:13]S(O)(=O)=O.N([O-])=O.[Na+]>O>[CH3:1][C:2]1[C:8]([N+:9]([O-:11])=[O:10])=[C:7]([CH3:12])[CH:6]=[CH:5][C:3]=1[OH:13]

Participants

5

Reactant 3

HCID 1118Sulfuric Acid2×HCID 133699632,4-Dimethyl-3-nitroanilineHCID 23668193Sodium Nitrite

Product 1

HCID 133699642,4-Dimethyl-3-nitrophenol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

2,4-dimethyl-3-nitroaniline (105.6 g) is added to a reaction mixture containing 300 ml of H2SO4 and 300 ml of H2O. The reaction mixture is stirred at a temperature of 105°-108° C. for one half hour and then cooled to 0° C. A solution of sodium nitrite (52.6 g) in H2O (124 ml) is added dropwise. After addition is complete the reaction mixture is poured into a 50% aqueous H2SO4 solution (2,000 ml) and refluxed for one and one half hours. The reaction mixture is cooled over the weekend to ambient temperature, and filtered leaving a yellow and black solid which is washed with H2O, dried and boiled with hexanes (8 l). The hexane extract is concentrated and filtered to obtain 65.4 grams of a yellow solid, M.P. 99°-101° C.

Workup

  1. additionAfter addition
  2. temperaturerefluxed for one and one half hours
  3. temperatureThe reaction mixture is cooled over the weekend to ambient temperature
  4. filtrationfiltered
  5. customleaving a yellow and black solid which
  6. washis washed with H2O
  7. customdried
  8. extractionThe hexane extract
  9. concentrationis concentrated
  10. filtrationfiltered

Sources & evidence

ORD record
ord-c04e21962f38481db62315f7c05e794b
Source dataset
uspto-grants-1984_12
Patent number
US04487779

Reaction notes

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