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

HRID 414429Notes

Reaction equation

HRID 414429 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)benzene

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a stirred solution of 154 g (1 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 water clear 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)
  5. customto yield 160 g (93%) of water clear liquid

Sources & evidence

ORD record
ord-6881de694ca04e9bad722370699530b7
Source dataset
uspto-grants-1988_12
Patent number
US04792208

Reaction notes

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