Water → 4-(Benzyloxy)benzene-1-sulfonyl chloride

HRID 352396

Reaktionsgleichung

Reaktionsgleichung von HRID 352396
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:15]([Cl:18])(Cl)=[O:16].O.C(OCC)(=[O:22])C>ClCCCl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([Cl:18])(=[O:16])=[O:22])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 24386Thionyl ChlorideHCID 70352Benzyl Phenyl Ether

Produkt 1

HCID 47383854-(Benzyloxy)benzene-1-sulfonyl chloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel2×

Versuchsvorschrift

To a suspension of 22.4 g (146 mmol) of sulfur trioxide/DMF complex in 60 mL of anhydrous 1,2-dichloroethane at room temperature, was added a solution of 30 g (162 mmol) of benzylphenyl ether in 30 mL of anhydrous 1,2-dichloroethane. The resulting mixture was warmed to reflux and maintained there for 1 hour, cooled to room temperature and 10.8 mL (146 mmol) of thionyl chloride added. The reaction was then warmed to 75 C for 1 hour, cooled in an ice bath, 50 mL of water slowly added, then ethyl acetate. The layers were separated, washed with saturated sodium bicarbonate, brine, dried with magnesium sulfate, filtered and stripped. The resulting solids were triturated with hexane to afford 24.5 g of pure 4-(Benzyloxy)benzenesulfonyl chloride.

Aufarbeitung

  1. temperatureThe resulting mixture was warmed
  2. temperatureto reflux
  3. temperaturemaintained there for 1 hour
  4. temperatureThe reaction was then warmed to 75 C for 1 hour
  5. temperaturecooled in an ice bath
  6. customThe layers were separated
  7. washwashed with saturated sodium bicarbonate, brine
  8. dry with materialdried with magnesium sulfate
  9. filtrationfiltered
  10. customThe resulting solids were triturated with hexane

Quellen und Nachweise

ORD-Eintrag
ord-be569f83d1ea421887b5ea785b7a15d0
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06747027B1

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