Isoamyl Nitrite → 2-Hydroxyimino-2-(3-phenoxyphenyl)acetonitrile

HRID 1070038Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1070038
[O-]CC.[Na+].[Na].[O:6]([C:13]1[CH:14]=[C:15]([CH2:19][C:20]#[N:21])[CH:16]=[CH:17][CH:18]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[N:22](OCCC(C)C)=[O:23]>C(O)C.C(OCC)C>[OH:23][N:22]=[C:19]([C:15]1[CH:16]=[CH:17][CH:18]=[C:13]([O:6][C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:14]=1)[C:20]#[N:21]

Komponenten

7

Edukt 4

HCID 8053Isoamyl NitriteHCID 40075m-Phenoxybenzyl cyanideHCID 2723922Sodium ethoxideHCID 5360545Sodium

Produkt 1

HCID 853082792-Hydroxyimino-2-(3-phenoxyphenyl)acetonitrileAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittel2×HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a solution of sodium ethoxide prepared from sodium (1.09 g) and ethanol (20 ml), a solution of 3-phenoxyphenylacetonitrile (8.30 g) in ethanol (15 ml) was added dropwise at 0° C., and then isoamyl nitrite (7.99 ml) was added dropwise. After stirring for 15 hours at room temperature, diethyl ether was added and the mixture was washed sequentially with 1N HCl, aqueous sodium bicarbonate and then saturated aqueous sodium chloride. The diethyl ether layer was dried (MgSO4), concentrated, and the residue was subjected to column chromatography on silica gel. The crystals obtained from a fraction eluted with ethyl acetate-hexane (1:4, v/v) were recrystallized with ethyl acetate-hexane to obtain 2-hydroxyimino-2-(3-phenoxyphenyl)acetonitrile (4.25 g, yield: 45%) as pale-yellow crystals. A mixture of the E- form and the Z- form. m.p. 124-125° C.

Aufarbeitung

  1. washthe mixture was washed sequentially with 1N HCl, aqueous sodium bicarbonate
  2. dry with materialThe diethyl ether layer was dried (MgSO4)
  3. concentrationconcentrated
  4. customThe crystals obtained from a fraction
  5. washeluted with ethyl acetate-hexane (1:4, v/v)
  6. customwere recrystallized with ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-4315ba764d5148efaf6776f8b73e386d
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06251926B1

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