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

HRID 973969Notes

Reaction equation

HRID 973969 reaction equation
[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+].ClCl>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]

Participants

5

Reactant 3

HCID 15666Ammonium thiocyanateHCID 24526ChlorineHCID 314052,6-Di-tert-butylphenol

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 2,6-di-tert-butylphenol (474g, 2.30 mole) and ammonium thiocyanate (76.12g, 4.83 mole) in methanol (1200ml) 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.

Workup

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

Sources & evidence

ORD record
ord-84e7c3f94b424b0e90c1783cc57a21f8
Source dataset
uspto-grants-1991_11
Patent number
US05066679

Reaction notes

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