Thionyl Chloride → 4-Chloro-2-methoxybenzoyl chloride

HRID 1037899Notes

Reaction equation

HRID 1037899 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[C:4]([O:11][CH3:12])[CH:3]=1.O=S(Cl)[Cl:15]>>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([Cl:15])=[O:7])=[C:4]([O:11][CH3:12])[CH:3]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 936824-Chloro-o-anisic acid

Product 1

HCID 221424504-Chloro-2-methoxybenzoyl chloride

Procedure

A solution of the 4-chloro-2-methoxybenzoic acid (0.24 g, 1.3 mmol) in 7 mL of SOCl2 was warmed to reflux and was allowed to stir for 2 hours. The mixture was cooled to ambient temperature and concentrated under reduced pressure. The crude material was diluted with 5 mL of toluene and concentrated under reduced pressure. This dilution with toluene and concentration was repeated two additional times to give the crude title compound which was used without additional purification or characterization.

Workup

  1. temperatureto reflux
  2. concentrationconcentrated under reduced pressure
  3. additionThe crude material was diluted with 5 mL of toluene
  4. concentrationconcentrated under reduced pressure
  5. concentrationThis dilution with toluene and concentration

Sources & evidence

ORD record
ord-c4c912257c3b4f38a6cc0dba31a36cdd
Source dataset
uspto-grants-2013_10
Patent number
US08546583B2

Reaction notes

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