Water → 2,6-Bis(1,1-dimethylethyl)-4-(methylthio)phenol

HRID 231589

Reaction equation

HRID 231589 reaction equation
[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([S:16][C:17]#N)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])[CH3:3].C(OP(OCC)OCC)C.O>CO>[CH3:4][C:2]([C:5]1[CH:6]=[C:7]([S:16][CH3:17])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:1])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 31215Triethyl phosphiteHCID 6192452,6-DI-Tert-butyl-4-thiocyanato-phenol

Product 1

HCID 144799522,6-Bis(1,1-dimethylethyl)-4-(methylthio)phenol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3,5-bis(1,1-dimethylethyl)-4-hydroxyphenylthiocyanate (238 g, 0.90 mole), triethylphosphite (225 g, 1.35 mole), water (200 g), and methanol (2000 ml) was stirred at reflux for two hours. Upon cooling, the mixture was concentrated in vacuo. The residue was triturated with water, and the solid was collected by filtration and air dried. Recrystallization from aqueous methanol gave the title compound, m.p. 69°-71°.

Workup

  1. temperatureat reflux for two hours
  2. temperatureUpon cooling
  3. concentrationthe mixture was concentrated in vacuo
  4. customThe residue was triturated with water
  5. filtrationthe solid was collected by filtration and air
  6. customdried
  7. customRecrystallization from aqueous methanol

Sources & evidence

ORD record
ord-eb54f59a4b2e411eb36221891cf989dc
Source dataset
uspto-grants-1989_07
Patent number
US04847305

Linked notes

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