Lithium hydroxide, monohydrate → 1-(Carboxy)-1-(4-methoxybenzylthio)cyclopropane

HRID 22517Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 22517
[C:1]([C:6]1([S:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[CH2:8][CH2:7]1)([O:3]CC)=[O:2].O.[OH-].[Li+]>C(O)C.O.O1CCCC1>[C:1]([C:6]1([S:9][CH2:10][C:11]2[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=2)[CH2:8][CH2:7]1)([OH:3])=[O:2]

Komponenten

6

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 224002171-(Carboethoxy)-1-(4-methoxybenzylthio)cyclopropane

Produkt 1

HCID 224002161-(Carboxy)-1-(4-methoxybenzylthio)cyclopropaneAusbeute 96,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Dissolve 1-(carboethoxy)-1-(4-methoxybenzylthio)cyclopropane (0.310 g, 1.16 mmol) in 95% ethanol (6 mL), water (3 mL), and tetrahydrofuran (6 mL). Treat with lithium hydroxide monohydrate (420 mg, 10 mmol). Stir at a gentle reflux for 6 hours and evaporate the solvent in vacuo. Add water (50 mL) and wash with ether (50 mL). Acidify the aqueous phase and extract into methylene chloride (50 mL). Dry (Na2SO4) and evaporate the solvent in vacuo to give 1-(carboxy)-1-(4-methoxybenzylthio)cyclopropane as a pale yellow solid (266 mg).

Aufarbeitung

  1. temperaturea gentle reflux for 6 hours
  2. customevaporate the solvent in vacuo
  3. washAdd water (50 mL) and wash with ether (50 mL)
  4. extractionextract into methylene chloride (50 mL)
  5. dry with materialDry (Na2SO4)
  6. customevaporate the solvent in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-912f4d8a34614dd5adb3cbdaf203a796
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05428158

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