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

Participants

Reaction Conditions

Reaction Steps

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 while powder, m.p. 61.5° -63° C. Analysis calc. for C15H21NSO:

Provenance & Evidence