2,2,3,3,3-Pentafluoropropanol → 2,2,3,3,3-Pentafluoropropyl p-Toluenesulfonate

HRID 1030442

Reaktionsgleichung

Reaktionsgleichung von HRID 1030442
[Cl-].[C:2]1([CH3:12])[CH:7]=[CH:6][C:5]([S:8]([O-:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[F:13][C:14]([F:21])([C:17]([F:20])([F:19])[F:18])[CH2:15]O.[OH-].[Na+]>O>[F:13][C:14]([F:21])([C:17]([F:20])([F:19])[F:18])[CH2:15][O:10][S:8]([C:5]1[CH:4]=[CH:3][C:2]([CH3:12])=[CH:7][CH:6]=1)(=[O:11])=[O:9]

Komponenten

5

Edukt 3

HCID 98722,2,3,3,3-PentafluoropropanolHCID 14798Sodium HydroxideHCID 22024621HCID 22024621, Verbindung

Produkt 1

HCID 27760172,2,3,3,3-Pentafluoropropyl p-ToluenesulfonateAusbeute 82,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To p-toluenesulfonate chloride (400.66 gm/2.10 mol) in water at 25° C. was added 2,2,3,3,3-pentafluoro-1-propanol (300.8 gm). The mixture was heated in a 5 liter, 3-neck separatory funnel type reaction flask, under mechanical stirring, to a temperature of 50° C. Sodium hydroxide (92.56 gm/2.31 mol) in 383 ml water(6M solution) was added dropwise to the reaction mixture via addition funnel over a period of 2.5 hours, keeping the temperature below 55° C. Upon completion of this addition, when the pH of the aqueous phase was approximately 6, the organic phase was drained from the flask while still warm, and allowed to cool to 25° C. The crude product was recrystallized from petroleum ether to afford white needles of 2,2,3,3,3-pentafluoropropyl-p-toluenesulfonate (500.7 gm/1.65 mol, 82.3%).

Aufarbeitung

  1. customthe temperature below 55° C
  2. additionUpon completion of this addition, when the pH of the aqueous phase
  3. temperaturewhile still warm
  4. temperatureto cool to 25° C
  5. customThe crude product was recrystallized from petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-7ba5a4df933744e38d7b69b935b8d5fa
Quelldatensatz
uspto-grants-1992_04
Patentnummer
US05106526

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