Phenolphthalein → Acetonitrile, [[4-(1,1-dimethylethyl)phenyl]thio]-

HRID 1731068

Reaktionsgleichung

Reaktionsgleichung von HRID 1731068
C1(S)C=CC=CC=1.Cl[CH2:9][C:10]#[N:11].[C:12]([C:16]1[CH:21]=[CH:20][C:19]([SH:22])=[CH:18][CH:17]=1)([CH3:15])([CH3:14])[CH3:13].C1C=CC2C(C3C=CC(O)=CC=3)(C3C=CC(O)=CC=3)OC(=O)C=2C=1>[OH-].[Na+].C(O)C.O>[C:12]([C:16]1[CH:17]=[CH:18][C:19]([S:22][CH2:9][C:10]#[N:11])=[CH:20][CH:21]=1)([CH3:15])([CH3:13])[CH3:14]

Komponenten

8

Edukt 4

HCID 4764PhenolphthaleinHCID 7856Chloroacetonitrile2×HCID 7969ThiophenolHCID 754544-Tert-Butylbenzenethiol

Produkt 1

HCID 21494992Acetonitrile, [[4-(1,1-dimethylethyl)phenyl]thio]-

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel2×HCID 14798Sodium HydroxideLösungsmittel2×

Versuchsvorschrift

The substituted phenylthioacetonitrile starting materials can be prepared by the reaction of the corresponding thiophenol with chloroacetonitrile in alcoholic sodium hydroxide. In a representative procedure, a solution of 100 grams of 4-tert-butylthiophenol and 45.3 grams chloroacetonitrile in 225 milliliters of 95 percent ethanol is stirred at room temperature while a solution of 24 grams sodium hydroxide in 36 milliliters water is added dropwise until the mixture remains alkaline to phenolphthalein. Slight spontaneous warming occurs during the addition. The mixture is then diluted with an equal volume of water and extracted twice with ether. The ether extract is washed with water, dried over sodium sulfate, and distilled, yielding the 2-(4-tert-butylphenylthio)acetonitrile as a liquid boiling at 153°-6° C. under a pressure of 4 millimeters of mercury.

Aufarbeitung

  1. additionis added dropwise until the mixture
  2. temperatureSlight spontaneous warming
  3. additionoccurs during the addition
  4. extractionextracted twice with ether
  5. extractionThe ether extract
  6. washis washed with water
  7. dry with materialdried over sodium sulfate
  8. distillationdistilled

Quellen und Nachweise

ORD-Eintrag
ord-fdf1cc8152bc4ff8b03d2bb123f50d7f
Quelldatensatz
uspto-grants-1976_11
Patentnummer
US03994976

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