Thionyl Chloride → 1-Chloro-2-(chloromethyl)-3-methylbenzene

HRID 1679895Notes

Reaction equation

HRID 1679895 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:3]=1[CH2:4]O.S(Cl)([Cl:13])=O>C1C=CC=CC=1>[Cl:13][CH2:4][C:3]1[C:6]([CH3:10])=[CH:7][CH:8]=[CH:9][C:2]=1[Cl:1]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 20579023(2-Chloro-6-methylphenyl)methanol

Product 1

HCID 200723601-Chloro-2-(chloromethyl)-3-methylbenzene

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The 2-chloro-6-methylbenzyl alcohol is dissolved in 100 ml of benzene, treated with 25 ml of thionyl chloride and the mixture is heated at reflux for 3 hours. Concentration of this mixture to dryness leaves a liquid which partly solidifies. The product containing liquid is decanted from the solid by-product and distilled to yield 7.8 g of alpha,2-dichloro-6-methyltoluene as a colorless liquid with bp. 118°-122° C./17-18 mm of Hg.

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux for 3 hours
  3. customConcentration of this mixture to dryness leaves a liquid which
  4. additionThe product containing liquid
  5. customis decanted from the solid by-product
  6. distillationdistilled

Sources & evidence

ORD record
ord-14633b8aac8f434ba8a665996dc66003
Source dataset
uspto-grants-1981_06
Patent number
US04271164

Reaction notes

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