Thionyl Chloride → HCID 21453018, compound

HRID 436646Notes

Reaction equation

HRID 436646 reaction equation
[Cl:1][C:2]([Cl:14])=[CH:3][O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9](O)=[O:10])=[CH:7][CH:6]=1.S(Cl)([Cl:17])=O>>[Cl:1][C:2]([Cl:14])=[CH:3][O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([Cl:17])=[O:10])=[CH:7][CH:6]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 19835260HCID 19835260, compound

Product 1

HCID 21453018HCID 21453018, compound

Procedure

A mixture containing 27.8 g. of 4-(2,2-dichlorovinyloxy)benzoic acid and 278 ml. of thionyl chloride was stirred and refluxed on a steam bath for 3 hours. The excess thionyl chloride was distilled off, first at atmospheric pressure and then at reduced pressure. Ethylene dichloride was added to the liquid residue and the solution evaporated in vacuo to remove the ethylene dichloride and remaining traces of thionyl chloride. There was thus obtained a quantitative yield of 4-(2,2-dichlorovinyloxy)benzoyl chloride as a pale yellow, non-volatile liquid.

Workup

  1. additionA mixture containing 27.8 g
  2. temperaturerefluxed on a steam bath for 3 hours
  3. distillationThe excess thionyl chloride was distilled off, first at atmospheric pressure
  4. additionEthylene dichloride was added to the liquid residue
  5. customthe solution evaporated in vacuo
  6. customto remove the ethylene dichloride

Sources & evidence

ORD record
ord-20dba12d45714163bab30ed4ec4c4d09
Source dataset
uspto-grants-1977_02
Patent number
US04009208

Reaction notes

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