Chloroacetonitrile → (4-Formyl-3,5-dimethyl-phenoxy)-acetonitrile

HRID 1514884Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1514884
[OH:1][C:2]1[CH:9]=[C:8]([CH3:10])[C:5]([CH:6]=[O:7])=[C:4]([CH3:11])[CH:3]=1.Cl[CH2:13][C:14]#[N:15].C([O-])([O-])=O.[Cs+].[Cs+]>CC(C)=O>[CH:6]([C:5]1[C:4]([CH3:11])=[CH:3][C:2]([O:1][CH2:13][C:14]#[N:15])=[CH:9][C:8]=1[CH3:10])=[O:7]

Komponenten

5

Edukt 3

HCID 7856ChloroacetonitrileHCID 10796Cesium carbonateHCID 5910722,6-Dimethyl-4-hydroxybenzaldehyde

Produkt 1

HCID 86651260(4-Formyl-3,5-dimethyl-phenoxy)-acetonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A mixture of 4-hydroxy-2,6-dimethyl-benzaldehyde (150 mg), chloroacetonitrile (0.1 mL), and Cs2CO3 (390 mg) in acetone (10 mL) was stirred at room temperature for 16 h. The mixture was concentrated, diluted with water, and extracted with EtOAc. The organic extracts were washed with brine, dried over Na2SO4, and concentrated in vacuo. Purification by column chromatography (SiO2, 3:1 hexane/EtOAc) gave (4-formyl-3,5-dimethyl-phenoxy)-acetonitrile.

Aufarbeitung

  1. concentrationThe mixture was concentrated
  2. additiondiluted with water
  3. extractionextracted with EtOAc
  4. washThe organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customPurification by column chromatography (SiO2, 3:1 hexane/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-d05e4297aa99421583d029300f3f0d0a
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08222248B2

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