Water → 2,6-Di-tert-butyl-4-mercaptophenol

HRID 483446Notes

Reaction equation

HRID 483446 reaction equation
[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([S:16]C#N)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])[CH3:3].O.C(P(CC)CC)C>CC(C)=O>[CH3:4][C:2]([C:5]1[CH:6]=[C:7]([SH:16])[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 27365TriethylphosphineHCID 6192452,6-DI-Tert-butyl-4-thiocyanato-phenol

Product 1

HCID 703702,6-Di-tert-butyl-4-mercaptophenolYield 86.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

3,5-bis(1,1-Dimethylethyl)-4-hydroxyphenyl thiocyanate (55 g, 0.209 mole) was dissolved in acetone (200 ml) under an argon atmosphere. Water (7.6 g, 0.42 mole) was added and the reaction cooled to 0° C. Triethylphosphine (24.7 g, 0.209 mole) was added dropwise over a period of 1 hour and the reaction was then allowed to warm to room temperature with stirring. The solution was concentrated, solvents removed, and the resulting oil purified by chromatography on silica. The fractions containing the thiol were combined, the solvents removed to yield a white powder which was recrystallized from methanol/water and dried to yield 43.3 g of the desired product. NMR confirmed the identity of the product.

Workup

  1. temperatureto warm to room temperature
  2. concentrationThe solution was concentrated
  3. customsolvents removed
  4. customthe resulting oil purified by chromatography on silica
  5. additionThe fractions containing the thiol
  6. customthe solvents removed
  7. customto yield a white powder which
  8. customwas recrystallized from methanol/water
  9. customdried

Sources & evidence

ORD record
ord-9c53c9b7d2d44dc482a4884742549f3b
Source dataset
uspto-grants-1993_07
Patent number
US05225444

Reaction notes

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