Water → Butanoic acid, 4-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]-

HRID 5500

Reaktionsgleichung

Reaktionsgleichung von HRID 5500
[OH-].[K+].[CH3:3][C:4]([C:7]1[CH:12]=[C:11]([SH:13])[CH:10]=[C:9]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:8]=1[OH:18])([CH3:6])[CH3:5].C([O:21][C:22](=[O:27])[CH2:23][CH2:24][CH2:25]Br)C.O>CC(C)=O>[CH3:6][C:4]([C:7]1[CH:12]=[C:11]([S:13][CH2:25][CH2:24][CH2:23][C:22]([OH:27])=[O:21])[CH:10]=[C:9]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:8]=1[OH:18])([CH3:3])[CH3:5]

Komponenten

6

Edukt 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 703702,6-Di-tert-butyl-4-mercaptophenolHCID 76300Ethyl 4-bromobutyrate

Produkt 1

HCID 9840255Butanoic acid, 4-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

Potassium hydroxide flakes (2.52 g, 0.045 mole) were added to a clear solution of 2,6-bis(1,1-dimethylethyl)-4-mercaptophenol (3.57 g, 0.0165 mole) and ethyl-4-bromo-butyrate (3.23 g, 0.0165 mole) in acetone (10 ml). Water (20 ml) was added and the solution stirred for 1.5 hours, the solvent removed on a rotary evaporator and water (50 ml) added, and the mixture was extracted with ethyl ether (3×75 ml). The aqueous layer was acidified with concentrated hydrochloric acid, extracted with ethyl ether (2×50 ml), the combined organic extracts were washed with water (50 ml), dried over sodium sulfate, filtered and the solvents removed, leaving an oil, which was purified by chromatography on silica, recrystallized from ethyl ether/Skellysolve B, filtered and the product dried in vacuo at room temperature for 12 hours, m.p. ca. 112°-113.5° C.

Aufarbeitung

  1. customthe solvent removed on a rotary evaporator and water (50 ml)
  2. additionadded
  3. extractionthe mixture was extracted with ethyl ether (3×75 ml)
  4. extractionextracted with ethyl ether (2×50 ml)
  5. washthe combined organic extracts were washed with water (50 ml)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customthe solvents removed
  9. customleaving an oil, which
  10. customwas purified by chromatography on silica
  11. customrecrystallized from ethyl ether/Skellysolve B
  12. filtrationfiltered
  13. customthe product dried in vacuo at room temperature for 12 hours

Quellen und Nachweise

ORD-Eintrag
ord-e382774d53ff40749e90ddad18853b83
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05244899

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