Toluene → Ethyl 4-chloro-3-nitrobenzoate

HRID 324722Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 324722
[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]

Komponenten

4

Edukt 2

HCID 1140TolueneHCID 73204-Chloro-3-nitrobenzoic acid

Produkt 1

HCID 1268247Ethyl 4-chloro-3-nitrobenzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24386Thionyl ChlorideLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-d3c691f72c4244a18370dbd818f1f067
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06218547B1

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