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

HRID 1199287Notes

Reaction equation

HRID 1199287 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-bd5d59b4880f4a139547753ab1e7509b
Source dataset
uspto-grants-1990_02
Patent number
US04900127

Reaction notes

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