Potassium Hydroxide → 3-[(4-Hydroxyphenyl)sulfanyl]-2,2-dimethylpropanoic acid

HRID 249536Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 249536
[CH3:1][C:2]([CH3:23])([CH2:7][S:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][Si](C(C)(C)C)(C)C)=[CH:11][CH:10]=1)[C:3]([O:5]C)=[O:4].[OH-].[K+]>O>[CH3:1][C:2]([CH3:23])([CH2:7][S:8][C:9]1[CH:10]=[CH:11][C:12]([OH:15])=[CH:13][CH:14]=1)[C:3]([OH:5])=[O:4]

Komponenten

4

Edukt 2

HCID 14797Potassium HydroxideHCID 22918963Methyl 2,2-dimethyl-3-(4'-tert-butyldimethylsilyloxyphenylthio)propionate

Produkt 1

HCID 183690193-[(4-Hydroxyphenyl)sulfanyl]-2,2-dimethylpropanoic acidAusbeute 82,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

Methyl 2,2-dimethyl-3-(4'-tert-butyldimethylsilyloxyphenylthio)propionate (7.09 g, 20 mmol) was added to KOH (6.73 g, 120 mmol) in 40 mL of H2O and the mixture was heated to reflux overnight. The reaction mixture was cooled to room temperature, diluted with 40 mL of H2O and extracted with ether. The aqueous layer was separated, acidified to pH=2 and extracted with ether (3×100 mL). The combined ether layers were dried over anhydrous MgSO4, filtered and evaporated to give 3.72 g (82%) of 2,2-dimethyl-3-(4'-hydroxyphenylthio)propionic acid as a white solid. 1H NMR (CD3COCD3) δ1.25 (s, 6H), 3.11 (s, 2H), 6.80 (d, 2H, J=8.4 Hz), 7.31 (d, 2H, J=8.7 Hz), 8.6 (br s, 1H, --OH); 13C NMR (CD3COCD3) δ25.13, 44.53, 47.63, 117.21, 127.46, 134.67, 158.18, 178.41.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureto reflux overnight
  3. extractionextracted with ether
  4. customThe aqueous layer was separated
  5. extractionextracted with ether (3×100 mL)
  6. dry with materialThe combined ether layers were dried over anhydrous MgSO4
  7. filtrationfiltered
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-210bb71fb6754b97bebba3e3bd2ca74c
Quelldatensatz
uspto-grants-1993_05
Patentnummer
US05214191

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