Benzenebutanoic acid, gamma-oxo-, methyl ester → methyl (4E)-4-hydroxyimino-4-phenylbutanoate

HRID 584348

Reaktionsgleichung

Reaktionsgleichung von HRID 584348
[C:1]([CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:16][OH:17].C([O-])(=O)C.[Na+]>CO>[OH:17]/[N:16]=[C:1](/[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)\[CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12]

Komponenten

5

Edukt 3

HCID 141190Benzenebutanoic acid, gamma-oxo-, methyl esterHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

Produkt 1

HCID 12137371methyl (4E)-4-hydroxyimino-4-phenylbutanoateAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of methyl 3-benzoylpropionate (15.0 g), hydroxylamine hydrochloride (6.50 g), sodium acetate (9.60 g) and methanol (150 ml) was heated under reflux for 8 hours. The reaction mixture was concentrated, and the residue was diluted with water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4), and then concentrated. The residue was subjected to column chromatography on silica gel, and methyl E-4-hydroxyimino-4-phenylbutyrate (14.7 g, yield 91%) was obtained as an oil from a fraction eluted with ethyl acetate-hexane (1:3, v/v).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 8 hours
  3. concentrationThe reaction mixture was concentrated
  4. additionthe residue was diluted with water
  5. extractionextracted with ethyl acetate
  6. washThe ethyl acetate layer was washed with water
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-ca5ef807c3f94844b8862ef5353e8fce
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06924300B2

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