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

HRID 973970Notes

Reaction equation

HRID 973970 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-mercaptophenol

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenylthiocyanate (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 and the solvents removed to yield a white powder. Recrystallization from methanol/water yielded, upon drying, 43.3 g of the title compound. The NMR spectrum 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
  8. customRecrystallization from methanol/water
  9. customyielded
  10. customupon drying

Sources & evidence

ORD record
ord-a001f2f7fc454bb3a0b13b8b585cd67c
Source dataset
uspto-grants-1991_11
Patent number
US05066679

Reaction notes

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