Thionyl Chloride → 1-(Chloromethyl)-4-(methylthio)benzene

HRID 730032

Reaktionsgleichung

Reaktionsgleichung von HRID 730032
[CH3:1][S:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7]O)=[CH:5][CH:4]=1.S(Cl)([Cl:13])=O>ClCCl>[Cl:13][CH2:7][C:6]1[CH:9]=[CH:10][C:3]([S:2][CH3:1])=[CH:4][CH:5]=1

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 592968[4-(Methylsulfanyl)phenyl]methanol

Produkt 1

HCID 701281-(Chloromethyl)-4-(methylthio)benzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

4-Methylsulfanylbenzyl alcohol (30.5 g; 0.2 mol) was dissolved in dichloromethane (180 ml). A solution of thionyl chloride (23.8 g; 0.2 mol) in dichloromethane (120 ml) was added dropwise to the initial charge, which was kept under reflux. The reaction mixture was stirred under reflux for a further 2 h. The solution was cooled to room temperature, washed with H2O (2×250 ml), dried over Na2SO4 and concentrated. The oily residue (6) was purified by column chromatography (Al2O3, CH2Cl2).

Aufarbeitung

  1. additioninitial charge
  2. temperatureunder reflux
  3. temperatureunder reflux for a further 2 h
  4. washwashed with H2O (2×250 ml)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe oily residue (6) was purified by column chromatography (Al2O3, CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-024e125b0bda4ea2b42a1e8a8e63da2f
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07582660B2

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