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

HRID 359729

Reaktionsgleichung

Reaktionsgleichung von HRID 359729
[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]

Komponenten

5

Edukt 3

HCID 962WaterHCID 27365TriethylphosphineHCID 6192452,6-DI-Tert-butyl-4-thiocyanato-phenol

Produkt 1

HCID 703702,6-Di-tert-butyl-4-mercaptophenol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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.

Aufarbeitung

  1. temperatureto warm to room temperature
  2. concentrationThe solution was concentrated
  3. customsolvents removed
  4. customthe resulting oil purified by chromatography on silica The fractions
  5. additioncontaining the thiol
  6. customthe solvents removed
  7. customto yield
  8. customa white powder Recrystallization from methanol/water
  9. customyielded
  10. customupon drying

Quellen und Nachweise

ORD-Eintrag
ord-ce4486e1877a46baa8697ee23aa3e536
Quelldatensatz
uspto-grants-1991_03
Patentnummer
US05002967

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