Reaktion #5587

Reaktionsgleichung

2,6-di-tert-butylphenol

ammonium thiocyanate

→

product

3,5-bis(1,1-dimethylethyl)-4-hydroxyphenylthiocyanate

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeTo a three-necked, round bottom 5 L flask, equipped with a mechanical stirrer, gas inlet
2. 2
   TemperaturMaintaining the temperature at 0° to 10° C.
3. 3
   Sonstigechlorine gas was slowly bubbled through the mixture for about 1 hour whereupon the reaction mixture
4. 4
   SonstigeAmmonia was then bubbled through the reaction for about 1-1/2 hours
5. 5
   Temperaturmaintaining the reaction mixture at a temperature of between 0° to 10° C
6. 6
   workup.STIRRINGThe reaction was stirred for an additional hour at 0° C.
7. 7
   workup.ADDITIONpoured into 2 L
8. 8
   workup.DISTILLATIONof cold distilled water and refrigerated overnight
9. 9
   SonstigeThe aqueous phase was decanted
10. 10
    Sonstigeprecipitated from water
11. 11
    Filtrationfiltered
12. 12
    Trocknendried for 2 days over phosphorous pentoxide
13. 13
    SonstigeThe resulting gummy yellow solid was recrystallized from pentane
14. 14
    Sonstigedried in vacuo

Vorschrift

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.

Quelle