Hydroxyamine hydrochloride → ethyl (2Z)-2-hydroxyimino-2-(4-methoxyphenyl)acetate

HRID 1070031Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1070031
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=O)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:5][CH:4]=1.Cl.[NH2:17][OH:18].C([O-])(=O)C.[Na+]>C(O)C>[OH:18]/[N:17]=[C:9](/[C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)\[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Komponenten

5

Edukt 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 2758864Ethyl 2-(4-methoxyphenyl)-2-oxoacetate

Produkt 1

HCID 11770071ethyl (2Z)-2-hydroxyimino-2-(4-methoxyphenyl)acetateAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of ethyl 4-methoxyphenylglyoxylate (15.0 g), hydroxylamine hydrochloride (6.00 g), sodium acetate (8.86 g) and ethanol (150 ml) was heated under reflux for 12 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 ethyl Z-2-hydroxyimino-2-(4-methoxyphenyl)acetate (8.99 g, yield 56%) was obtained as crystals from a fraction eluted with ethyl acetate-hexane (1:2, v/v). Recrystallization from ethyl acetate-hexane gave colorless crystals. m.p. 81-82° C.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 12 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-4e87c11be8904b4da319f4ba341f3133
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06251926B1

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