Nitric Acid → Benzenesulfonic acid, 4-methyl-3-nitro-

HRID 1440726Notes

Reaction equation

HRID 1440726 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([OH:10])(=[O:9])=[O:8])=[CH:3][CH:2]=1.[N+:12]([O-])([OH:14])=[O:13]>O>[CH3:11][C:1]1[CH:2]=[CH:3][C:4]([S:7]([OH:10])(=[O:8])=[O:9])=[CH:5][C:6]=1[N+:12]([O-:14])=[O:13]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 6101p-Toluenesulfonic acid

Product 1

HCID 66795Benzenesulfonic acid, 4-methyl-3-nitro-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 25.0 g of 4-toluenesulfonic acid and 95 ml of concentrated nitric acid was heated on a steam bath for 30 minutes during which time the solution turned deep red and gas was evolved. The reaction was allowed to cool to room temperature, poured into 250 ml of water and concentrated. An additional 30 ml of water was added and the solution again concentrated. This procedure was repeated three additional times. The resulting oil was dissolved in 30 ml of water and neutralized with the addition of 11.04 g of sodium bicarbonate. After the bubbling stopped the solution was concentrated to yield a white powder which was triturated with 300 ml of isopropanol, isolated via vacuum filtration and air dried to yield 28.9 g of the desired 4-methyl-3-nitrobenzenesulfonic acid, sodium salt.

Workup

  1. concentrationconcentrated
  2. additionAn additional 30 ml of water was added
  3. concentrationthe solution again concentrated
  4. dissolutionThe resulting oil was dissolved in 30 ml of water
  5. additionneutralized with the addition of 11.04 g of sodium bicarbonate
  6. concentrationwas concentrated
  7. customto yield a white powder which
  8. customwas triturated with 300 ml of isopropanol
  9. customisolated via vacuum filtration and air
  10. customdried

Sources & evidence

ORD record
ord-9becb1b48a6c4e3d8e0de0d43d83cad7
Source dataset
uspto-grants-1996_03
Patent number
US05500405

Reaction notes

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