Thionyl Chloride → 3-Methyl-6-(phenylthio)-benzyl chloride

HRID 435607Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 435607
[CH3:1][C:2]1[CH:3]=[C:4]([C:7]([S:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:8][CH:9]=1)[CH2:5]O.S(Cl)([Cl:19])=O>C1C=CC=CC=1>[CH3:1][C:2]1[CH:3]=[C:4]([C:7]([S:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:8][CH:9]=1)[CH2:5][Cl:19]

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 12539099HCID 12539099, Verbindung

Produkt 1

HCID 125391003-Methyl-6-(phenylthio)-benzyl chloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

570.7 g of 3-methyl-6-(phenylthio)-benzyl alcohol are dissolved in 1.5 litres of benzene and heated under reflux. There are added dropwise thereto within 45 minutes 352 ml of thionyl chloride and the mixture is boiled for a further 90 minutes. Then the mixture is concentrated under reduced pressure and there is obtained 3-methyl-6-(phenylthio)-benzyl chloride as a red-brown oil. 194 g of potassium cyanide in 250 ml of water are heated under reflux for 17 hours under an argon atmosphere with 616.9 g of 3-methyl-6-(phenylthio)-benzyl chloride in 900 ml of ethanol. Then the ethanol is distilled off under reduced pressure, the residue then diluted with water and extracted with ether. The extracts are washed with water, dried over sodium sulphate and evaporated. There is obtained 3-methyl-6-(phenylthio)-phenylacetonitrile as an oil.

Aufarbeitung

  1. temperatureheated
  2. temperatureunder reflux
  3. additionThere are added dropwise
  4. concentrationThen the mixture is concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-402513f8bf0e4e6c8b30b42861267ed9
Quelldatensatz
uspto-grants-1977_02
Patentnummer
US04006145

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