Thionyl Chloride → 4-Allyloxybenzoyl chloride

HRID 436648Notes

Reaction equation

HRID 436648 reaction equation
[CH2:1]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9](O)=[O:10])=[CH:7][CH:6]=1)[CH:2]=[CH2:3].S(Cl)([Cl:16])=O>>[CH2:1]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([Cl:16])=[O:10])=[CH:7][CH:6]=1)[CH:2]=[CH2:3]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 4606904-(Prop-2-en-1-yloxy)benzoic acid

Product 1

HCID 117901374-Allyloxybenzoyl chloride

Procedure

A mixture containing 29.9 g. of 4-allyloxybenzoic acid and 250 ml. of thionyl chloride was stirred and refluxed for 90 minutes and the excess thionyl distilled off, first at atmospheric pressure and then at reduced pressure. Ethylene dichloride was added and the solution evaporated in vacuo to remove the ethylene dichloride and remaining traces of thionyl chloride to give a quantitative yield of 4-allyloxybenzoyl chloride.

Workup

  1. additionA mixture containing 29.9 g
  2. temperaturerefluxed for 90 minutes
  3. distillationthe excess thionyl distilled off, first at atmospheric pressure
  4. additionEthylene dichloride was added
  5. customthe solution evaporated in vacuo
  6. customto remove the ethylene dichloride

Sources & evidence

ORD record
ord-682f9f56768141e99581284105bbd55c
Source dataset
uspto-grants-1977_02
Patent number
US04009208

Reaction notes

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