Lithium Hydroxide → (+/-)-trans-2-(4-Chlorophenyl)-4-oxocyclohexanecarboxylic acid

HRID 644938

Reaktionsgleichung

Reaktionsgleichung von HRID 644938
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:13][C:12](=[O:14])[CH2:11][CH2:10][C@H:9]2[C:15]([O:17]C)=[O:16])=[CH:4][CH:3]=1.[OH-].[Li+].Cl.[Cl-].[Na+].O>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]2[CH2:13][C:12](=[O:14])[CH2:11][CH2:10][C@H:9]2[C:15]([OH:17])=[O:16])=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 3939Lithium HydroxideHCID 68516321Methyl trans-2-(4-chlorophenyl)-4-oxocyclohexanecarboxylateHCID 131718760Hydrochloric acid brine

Produkt 1

HCID 21017822(+/-)-trans-2-(4-Chlorophenyl)-4-oxocyclohexanecarboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A stirred mixture of methyl trans-2-(4-chlorophenyl)-4-oxocyclohexanecarboxylate (1.05 g, 3.94 mmol) and 1 N lithium hydroxide (5.91 mL, 5.91 mmol) in tetrahydrofuran (5 mL) was heated at reflux for approximately 1 h. After cooling to room temperature, the reaction mixture was poured into 1 N hydrochloric acid/brine (1:1) and extracted three times with methylene chloride. The combined organic extracts were washed with brine, dried (MgSO4) and concentrated in vacuo. The crude title compound was used without further purification in the subsequent reaction.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for approximately 1 h
  3. extractionextracted three times with methylene chloride
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe crude title compound was used without further purification in the subsequent reaction

Quellen und Nachweise

ORD-Eintrag
ord-31158a1a8cab436c8b035ad7fd3e293e
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07700778B2

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