Toluene → Ethyl 4-chloro-3-nitrobenzoate

HRID 1633587Notes

Reaction equation

HRID 1633587 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[C:14]1(C)C=CC=C[CH:15]=1>S(Cl)(Cl)=O>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH2:14][CH3:15])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 1140TolueneHCID 73204-Chloro-3-nitrobenzoic acid

Product 1

HCID 1268247Ethyl 4-chloro-3-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

4-chloro-3-nitrobenzoic acid (40.0 g, 0.2 mol) was refluxed in thionyl chloride (150 ml) for 6 hours. After cooling toluene (50 ml) was added and the mixture was evaporated to dryness. Abs. ethanol (500 ml) was added to the cooled residue, and the resulting mixture was refluxed overnight. The excess of ethanol was removed under reduced pressure and the product crystallized upon addition of aqueous sodium bicarbonate (1M). Yield: 42.5 g (93%).

Workup

  1. additionwas added
  2. customthe mixture was evaporated to dryness
  3. additionethanol (500 ml) was added to the cooled residue
  4. temperaturethe resulting mixture was refluxed overnight
  5. customThe excess of ethanol was removed under reduced pressure
  6. customthe product crystallized upon addition of aqueous sodium bicarbonate (1M)

Sources & evidence

ORD record
ord-88c2ed341a294bcb9efaece5f5da35df
Source dataset
uspto-grants-2003_01
Patent number
US06503925B1

Reaction notes

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