Phosphorus oxychloride → Ethyl 4-(chlorosulfonyl)benzoate

HRID 1983203

Reaktionsgleichung

Reaktionsgleichung von HRID 1983203
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([S:12]([O-:15])(=O)=[O:13])=[CH:8][CH:7]=1)=[O:5])[CH3:2].[K+].O=P(Cl)(Cl)[Cl:19]>C(#N)C.S1(CCCC1)(=O)=O>[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([S:12]([Cl:19])(=[O:15])=[O:13])=[CH:8][CH:7]=1)=[O:5])[CH3:2]

Komponenten

5

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 23668296Potassium 4-ethoxycarbonylbenzenesulfonate

Produkt 1

HCID 3667622Ethyl 4-(chlorosulfonyl)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 31347SulfolaneLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

A round bottom flask, fitted with a magnetic stir bar and a hose adapter connected to a source of nitrogen gas, was charged with a solution of potassium 4-ethoxycarbonylbenzenesulfonate (75.1 g) dissolved in a 3:1 (v/v) mixture of acetonitrile (300 mL) and sulfolane (100 mL). As the solution was stirred, POCl3 (55 mL) was added slowly and the stirring mixture was heated at 75° C. under a nitrogen atmosphere for 3 hours. The heterogeneous reaction mixture was allowed to cool to room temperature and was then concentrated using a rotary evaporator. The flask was then cooled in an ice bath and ice was added to the mixture in the flask. The product crystallized as a white solid and was filtered and washed with cold deionized water. The product was dried under vacuum at room temperature and 3 mmHg for 2 hours to afford 76 g of white solid.

Aufarbeitung

  1. customA round bottom flask, fitted with a magnetic stir bar and a hose adapter
  2. temperatureto cool to room temperature
  3. concentrationwas then concentrated
  4. customa rotary evaporator
  5. temperatureThe flask was then cooled in an ice bath
  6. additionice was added to the mixture in the flask
  7. customThe product crystallized as a white solid
  8. filtrationwas filtered
  9. washwashed
  10. customThe product was dried under vacuum at room temperature

Quellen und Nachweise

ORD-Eintrag
ord-d6068e942c534735b5d4631a44f5b301
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07541389B2

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