Ammonium thiocyanate → 2,6-DI-Tert-butyl-4-thiocyanato-phenol

HRID 231585

Reaktionsgleichung

Reaktionsgleichung von HRID 231585
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].[S-:16][C:17]#[N:18].[NH4+]>CO>[CH3:12][C:11]([C:7]1[CH:8]=[C:9]([S:16][C:17]#[N:18])[CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]=1[OH:15])([CH3:14])[CH3:13]

Komponenten

4

Edukt 2

HCID 15666Ammonium thiocyanateHCID 314052,6-Di-tert-butylphenol

Produkt 1

HCID 6192452,6-DI-Tert-butyl-4-thiocyanato-phenol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of 2,6-di-tert-butylphenol (474 g, 2.30 mole) and ammonium thiocyanate (76.12 g, 4.83 mole) in methanol (1200 ml) was stirred with cooling at 0° C. While the temperature was maintained at 0° to 10° C., chlorine gas was slowly bubbled through the mixture for about 1 hour, during which time the reaction mixture became a heterogeneous yellow color. Ammonia was then bubbled through the mixture for about 1.5 hours, during which time the reaction mixture was maintained at a temperature of between 0° to 10° C. The reaction was stirred for an additional hour at 0° C., poured into 2 liters of cold distilled water and refrigerated overnight. The aqueous phase was decanted, and the solid was taken up in methanol, precipitated by addition of water, filtered, and dried for 2 days over phosphorus pentoxide. The resulting gummy yellow solid was recrystallized from pentane and dried in vacuo to yield the product as a white powder, m.p. 61.5° -63° C.

Aufarbeitung

  1. temperatureWhile the temperature was maintained at 0° to 10° C.
  2. customchlorine gas was slowly bubbled through the mixture for about 1 hour, during which time the reaction mixture
  3. customAmmonia was then bubbled through the mixture for about 1.5 hours, during which time the reaction mixture
  4. temperaturewas maintained at a temperature of between 0° to 10° C
  5. stirringThe reaction was stirred for an additional hour at 0° C.
  6. additionpoured into 2 liters
  7. distillationof cold distilled water and refrigerated overnight
  8. customThe aqueous phase was decanted
  9. customprecipitated by addition of water
  10. filtrationfiltered
  11. dry with materialdried for 2 days over phosphorus pentoxide
  12. customThe resulting gummy yellow solid was recrystallized from pentane
  13. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-51a40d6ca47c432488ebc7df1dbf4bb6
Quelldatensatz
uspto-grants-1989_07
Patentnummer
US04847305

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