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

HRID 5491

Reaktionsgleichung

Reaktionsgleichung von HRID 5491
[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

To a three-necked, round bottom 5 L flask, equipped with a mechanical stirrer, gas inlet, thermometer and gas inlet, thermometer and gas outlet, was added 2,6-di-tert-butylphenol (474 g, 2.30 mole), ammonium thiocyanate (76.12 g, 4.83 mole) and methanol (1200 ml). The reaction mixture was stirred and cooled to 0° C. in an ice/salt bath. Maintaining the temperature at 0° to 10° C., chlorine gas was slowly bubbled through the mixture for about 1 hour whereupon the reaction mixture was a heterogeneous yellow color. Ammonia was then bubbled through the reaction for about 1-1/2 hours, maintaining the reaction mixture at a temperature of between 0° to 10° C. The reaction was stirred for an additional hour at 0° C., poured into 2 L of cold distilled water and refrigerated overnight. The aqueous phase was decanted and the solid taken up in methanol, precipitated from water, filtered and dried for 2 days over phosphorous 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. customTo a three-necked, round bottom 5 L flask, equipped with a mechanical stirrer, gas inlet
  2. temperatureMaintaining the temperature at 0° to 10° C.
  3. customchlorine gas was slowly bubbled through the mixture for about 1 hour whereupon the reaction mixture
  4. customAmmonia was then bubbled through the reaction for about 1-1/2 hours
  5. temperaturemaintaining the reaction mixture at a temperature of between 0° to 10° C
  6. stirringThe reaction was stirred for an additional hour at 0° C.
  7. additionpoured into 2 L
  8. distillationof cold distilled water and refrigerated overnight
  9. customThe aqueous phase was decanted
  10. customprecipitated from water
  11. filtrationfiltered
  12. dry with materialdried for 2 days over phosphorous pentoxide
  13. customThe resulting gummy yellow solid was recrystallized from pentane
  14. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-cb03feb9a3734441aae6f712cf1f69a9
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05244899

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