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

HRID 1461211Notes

Reaction equation

HRID 1461211 reaction equation
[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>C1C=CC=CC=1>[CH3:1][S:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][Cl:13])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 24386Thionyl Chloride2×HCID 592968[4-(Methylsulfanyl)phenyl]methanol

Product 1

HCID 701281-(Chloromethyl)-4-(methylthio)benzeneYield 93%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a stirred solution of 154 g (1.0 mol) of 4-methylmercaptobenzyl alcohol in 1 liter of dry benzene was added dropwise 80 mL (1.1 mol) of thionyl chloride. The mixture immediately turned blue. After the addition of the thionyl chloride was completed, the mixture was heated at reflux for 2 hours. After cooling, the benzene and excess thionyl chloride were distilled at ambient pressure. The product was distilled in vacuo at 105° C. (0.5 mm), to yield 160 g (93%) of a colorless liquid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 2 hours
  3. temperatureAfter cooling
  4. distillationthe benzene and excess thionyl chloride were distilled at ambient pressure
  5. distillationThe product was distilled in vacuo at 105° C. (0.5 mm)

Sources & evidence

ORD record
ord-9fbf3e9ef8f7467988af19e222882ae6
Source dataset
uspto-grants-1991_12
Patent number
US05075043

Reaction notes

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