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

HRID 1086454Notes

Reaction equation

HRID 1086454 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

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 2,6di-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 h the reaction for about 11/2 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. Analysis calc. for C15H21NSO: Theory: C, 68.40; H, 8.03; N, 5.32; S, 12.17. Found: C, 68.85; H, 8.05; N, 5.29; S, 12.12.

Workup

  1. customTo a three-necked, round bottom 5 L flask, equipped with a mechanical stirrer, gas inlet
  2. customwas slowly bubbled through the mixture for about 1 hour whereupon the reaction mixture
  3. customAmmonia was then bubbled h the reaction for about 11/2 hours
  4. temperaturemaintaining the reaction mixture 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 L
  7. distillationof cold distilled water and refrigerated overnight
  8. customThe aqueous phase was decanted
  9. customprecipitated from water
  10. filtrationfiltered
  11. dry with materialdried for 2 days over phosphorous pentoxide
  12. customThe resulting gummy yellow solid was recrystallized from pentane
  13. customdried in vacuo

Sources & evidence

ORD record
ord-628fa893a1774a2fac043dc2c59e4be7
Source dataset
uspto-grants-1991_07
Patent number
US05030642

Reaction notes

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