Water → Propanoic acid, 2-[[(4-methoxyphenyl)methyl]thio]-2-methyl-

HRID 2395985Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2395985
[C:1]([C:6]([S:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)([CH3:8])[CH3:7])([O:3]CC)=[O:2].O.O1CCCC1.[OH-].[K+]>C(O)C>[C:1]([C:6]([S:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=1)([CH3:7])[CH3:8])([OH:3])=[O:2]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 19974022HCID 19974022, Verbindung

Produkt 1

HCID 10421773Propanoic acid, 2-[[(4-methoxyphenyl)methyl]thio]-2-methyl-Ausbeute 81,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Dissolve 2-(carboethoxy)-2-(4-methoxybenzylthio)propane (1.05 g, 3.91 mmol)in a mixture of 95% ethanol (18 mL), water (9 mL) and tetrahydrofuran (10 mL). Add potassium hydroxide (1.4 g, 25 mmol) and stir at room temperaturefor 2 hours then at 55° C. for 1 hour. Evaporate the solvent in vacuo and partition between water (50 mL) and ether (50 mL). Acidify to pH1 with concentrated hydrochloric acid and extract into methylene chloride (50 mL). Dry (Na2SO4) and evaporate the solvent in vacuo to give 2-(carboxy)-2-(4-methoxybenzylthio)propane as a tan solid (763 mg).

Aufarbeitung

  1. customEvaporate the solvent in vacuo
  2. custompartition between water (50 mL) and ether (50 mL)
  3. extractionAcidify to pH1 with concentrated hydrochloric acid and extract into methylene chloride (50 mL)
  4. dry with materialDry (Na2SO4)
  5. customevaporate the solvent in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9d70bcebcb2847dfaec7658445293f50
Quelldatensatz
uspto-grants-1996_02
Patentnummer
US05491142

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