Toluene → Ethyl 4-chloro-3-nitrobenzoate

HRID 49805

Reaction equation

HRID 49805 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-845d090488194370a30c5357d06afd4a
Source dataset
uspto-grants-2004_03
Patent number
US06710044B2

Linked notes

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