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

HRID 2291432Notes

Reaction equation

HRID 2291432 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 Chloride3×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 mol) of 4-methylmercaptobenzyl alcohol in 1 liter of dry bensene 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. distillationwere distilled at ambient pressure
  4. distillationThe product was distilled in vacuo at 105° C. (0.5 mm)

Sources & evidence

ORD record
ord-baff32a420a34206a480f7fc4bd58557
Source dataset
uspto-grants-1989_01
Patent number
US04796971

Reaction notes

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