Ammonium thiocyanate → HCID 20033901, compound

HRID 231592Notes

Reaction equation

HRID 231592 reaction equation
[C:1]([C:5]1[CH:11]=[C:10]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:8]([OH:9])=[CH:7][C:6]=1[OH:16])([CH3:4])([CH3:3])[CH3:2].[S-:17][C:18]#N.[NH4+]>CO>[CH3:13][C:12]([C:10]1[CH:11]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]([OH:16])=[C:7]([S:17][CH3:18])[C:8]=1[OH:9])([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 15666Ammonium thiocyanateHCID 793371,3-Benzenediol, 4,6-bis(1,1-dimethylethyl)-

Product 1

HCID 20033901HCID 20033901, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4,6-di-t-butylresorcinol (25.0 g, 112 mmole) and ammonium thiocyanate (18.0 g, 235 mmole) in methanol (100 ml) was stirred for 24 hours. The mixture was cooled to 0° and chlorine gas was bubbled through the solution for one hour. After the mixture was stirred for an additional hour at 0°, ammonia gas was bubbled through for one hour. A solid was removed by filtration and the filrate was concentrated in vacuo. Chromatography on silica gel and recrystallization from hexane gave the title compound.

Workup

  1. temperatureThe mixture was cooled to 0°
  2. customchlorine gas was bubbled through the solution for one hour
  3. stirringAfter the mixture was stirred for an additional hour at 0°
  4. customammonia gas was bubbled through for one hour
  5. customA solid was removed by filtration
  6. concentrationthe filrate was concentrated in vacuo
  7. customChromatography on silica gel and recrystallization from hexane

Sources & evidence

ORD record
ord-a5631356438f4de699410a44fb0b1a6f
Source dataset
uspto-grants-1989_07
Patent number
US04847305

Reaction notes

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