Lithium hydroxide, monohydrate → 4-(4-Chlorophenyl)-4-(methoxyimino)butanoic acid

HRID 423072Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 423072
O.[OH-].[Li+].[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[N:19][O:20][CH3:21])[CH2:12][CH2:13][C:14]([O:16]CC)=[O:15])=[CH:7][CH:6]=1>O.C1COCC1.C(O)C.CCOC(C)=O>[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[N:19][O:20][CH3:21])[CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:7][CH:6]=1

Komponenten

7

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 86632052Ethyl 4-(4-chlorophenyl)-4-(methoxyimino)butanoate2×

Produkt 1

HCID 866320534-(4-Chlorophenyl)-4-(methoxyimino)butanoic acidAusbeute 69,1 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

Lithium hydroxide monohydrate (9.59 g, 228.57 mmol) was added to ethyl 4-(4-chlorophenyl)-4-(methoxyimino)butanoate (Intermediate 52) (12.33 g, 45.71 mmol) in water (25.4 mL), THF (102 mL) and ethanol (102 mL). The resulting solution was stirred at 20° C. for 1 day. The reaction mixture was diluted with EtOAc (200 mL) and washed with water (200 mL). The aqueous was adjusted to pH5 with 1M citric acid solution then extracted with EtOAc (3×150 mL). The organic extracts were washed with saturated brine (25 mL) then dried over MgSO4, filtered and evaporated to afford desired product 4-(4-chlorophenyl)-4-(methoxyimino)butanoic acid (7.63 g, 69.1%) as a light yellow solid.

Aufarbeitung

  1. washwashed with water (200 mL)
  2. extractionthen extracted with EtOAc (3×150 mL)
  3. washThe organic extracts were washed with saturated brine (25 mL)
  4. dry with materialthen dried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-c558eee4cfbc47ab816ab9469084dc81
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101623B2

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