4-Toluenesulfonyl chloride → (Z)-4-(4-Chlorophenyl)-2-buten-1-ol 4-methylbenzenesulfonate

HRID 464030Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 464030
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]/[CH:9]=[CH:10]\[CH2:11][OH:12])=[CH:4][CH:3]=1.[OH-:13].[K+].[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1>CCOCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8]/[CH:9]=[CH:10]\[CH2:11][OH:12])=[CH:6][CH:7]=1.[CH3:25][C:15]1[CH:20]=[CH:19][C:18]([S:21]([O-:23])(=[O:22])=[O:13])=[CH:17][CH:16]=1

Komponenten

5

Edukt 3

HCID 73974-Toluenesulfonyl chlorideHCID 14797Potassium HydroxideHCID 13660260HCID 13660260, Verbindung

Produkt 1

HCID 131714350(Z)-4-(4-Chlorophenyl)-2-buten-1-ol 4-methylbenzenesulfonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

Dissolve 7.3 g (0.04 mole) of (Z)-4-(4-chlorophenyl)but-2-en-ol in 100 ml of anhydrous ether. Add 3.2 g (0.05 mole) of powdered 86% KOH. Stir and cool the mixture in ice bath while adding a solution of 8.4 g (0.044 mole) of p-toluenesulfonyl chloride in 50 ml of anhydrous ether. Slowly warm the reaction mixture to room temperature and stir at room temperature for 16 hours. Remove the solid by filtration. Wash the filtrate with saturated aqueous sodium bicarbonate, H2O. Dry, evaporate, and recrystallize from cyclohexane to yield the title compound.

Aufarbeitung

  1. temperaturecool the mixture in ice bath
  2. stirringstir at room temperature for 16 hours
  3. customRemove the solid
  4. filtrationby filtration
  5. washWash the filtrate with saturated aqueous sodium bicarbonate, H2O
  6. customDry
  7. customevaporate
  8. customrecrystallize from cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-c561988f1b4741a29d719acbe2eb3f19
Quelldatensatz
uspto-grants-1985_10
Patentnummer
US04545995

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