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

HRID 1086468

Reaktionsgleichung

Reaktionsgleichung von HRID 1086468
[OH-:1].[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].[OH2:19]>CC(C)=O>[CH3:6][C:4]([C:7]1[CH:12]=[C:11]([S:13][CH2:3][CH2:4][CH2:7][C:8]([OH:19])=[O:1])[CH:10]=[C:9]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:8]=1[OH:18])([CH3:3])[CH3:5]

Komponenten

5

Edukt 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 703702,6-Di-tert-butyl-4-mercaptophenol

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, 0.015 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. The organic layer was extracted with ethyl ether (3×75 ml). The aqueous layer was acidified with concentrated hydrochloric acid, extracted with ethyl ether (2×50 ml), 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. Analysis calc. for C18H28O3S(324.48): Calc.: C, 66.63; H, 8.70; S, 9.88. Found: C, 66.71; H, 8.74; S, 9.57.

Aufarbeitung

  1. customthe solvent removed on a rotary evaporator and water (50 ml)
  2. additionadded
  3. extractionThe organic layer was extracted with ethyl ether (3×75 ml)
  4. extractionextracted with ethyl ether (2×50 ml)
  5. washwashed 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-eefb5af6c323492a9577d1767061c3d1
Quelldatensatz
uspto-grants-1991_07
Patentnummer
US05030642

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