Thionyl Chloride → (3-Methoxyphenyl)acetonitrile

HRID 35598

Reaktionsgleichung

Reaktionsgleichung von HRID 35598
S(Cl)(Cl)=O.[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH2:13][C:14]([NH2:16])=O)[CH:10]=[CH:11][CH:12]=1>CN(C)C=O>[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH2:13][C:14]#[N:16])[CH:10]=[CH:11][CH:12]=1

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 27749732-(3-Methoxyphenyl)acetamide

Produkt 1

HCID 88310(3-Methoxyphenyl)acetonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Thionyl chloride (1249 ml) was added dropwise to dry dimethylformamide (400 ml) stirring at 0°-5° C. under nitrogen over a period of about 2 hours. 3-Methoxyphenylacetamide (403.7 g) was added portionwise over a period of 45 minutes to the above solution under nitrogen maintaining the temperature between 0°-5° C. The reaction mixture was then stirred at 0°-5° C. for a further 2 hours. The reaction mixture was poured carefully onto ice/water (6 l). The aqueous mixture was extracted with ether. The extracts were washed with water, dried over magnesium sulphate and evaporated in vacuo to give a red liquid. The crude product was distilled (110°-112° C./12 mm Hg) to give 3-methoxyphenylacetonitrile.

Aufarbeitung

  1. stirringThe reaction mixture was then stirred at 0°-5° C. for a further 2 hours
  2. additionThe reaction mixture was poured carefully onto ice/water (6 l)
  3. extractionThe aqueous mixture was extracted with ether
  4. washThe extracts were washed with water
  5. dry with materialdried over magnesium sulphate
  6. customevaporated in vacuo
  7. customto give a red liquid
  8. distillationThe crude product was distilled (110°-112° C./12 mm Hg)

Quellen und Nachweise

ORD-Eintrag
ord-9c9dcda28fe244a7982077b1f6608d72
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04767769

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