Hydrochloric Acid → methyl E-2-hydroxyimino-2-(3-phenoxylphenyl)acetate

HRID 2299713Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2299713
[OH:1][N:2]=[C:3]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:7]=1)[C:4]#N.[OH-:19].[K+].[CH2:21]([OH:23])C.Cl>O>[OH:1]/[N:2]=[C:3](/[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:7]=1)\[C:4]([O:23][CH3:21])=[O:19]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14797Potassium HydroxideHCID 853082792-Hydroxyimino-2-(3-phenoxyphenyl)acetonitrile

Produkt 1

HCID 86589771methyl E-2-hydroxyimino-2-(3-phenoxylphenyl)acetateAusbeute 33 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 2-hydroxyimino-2-(3-phenoxyphenyl)acetonitrile (3.00 g), potassium hydroxide (3.40 g), ethanol (15 ml) and water (15 ml) was heated under reflux for 24 hours. The reaction mixture was acidified with 1 N HCl, and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride, dried (MgSO4) and then concentrated. The reaction mixture was dissolved in methanol (30 ml), admixed with concentrated sulfuric acid (a catalytic amount), and then heated under reflux for 24 hours. The reaction mixture was combined with aqueous sodium bicarbonate and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride, dried (MgSO4) and then concentrated. The residue was subjected to column chromatography on silica gel to obtain methyl Z-2-hydroxyimino-2-(3-phenoxyphenyl)acetate (1.14 g, yield 33%) as an oil from a fraction eluted with ethyl acetate-hexane (1:2, v/v).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 24 hours
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. dissolutionThe reaction mixture was dissolved in methanol (30 ml), admixed with concentrated sulfuric acid (a catalytic amount), and
  8. temperaturethen heated
  9. temperatureunder reflux for 24 hours
  10. extractionextracted with ethyl acetate
  11. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride
  12. dry with materialdried (MgSO4)
  13. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-67c53a2e08644fa7b01b9d74d6be868a
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06495581B1

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