Thionyl Chloride → 5-Chloro-2-methoxybenzoyl chloride

HRID 452952Notes

Reaction equation

HRID 452952 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6]([CH:10]=1)[C:7](O)=[O:8].S(Cl)([Cl:15])=O>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6]([CH:10]=1)[C:7]([Cl:15])=[O:8]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 769705-Chloro-o-anisic acid

Product 1

HCID 123841765-Chloro-2-methoxybenzoyl chloride

Procedure

A mixture of 5-chloro-2-methoxybenzoic acid (0.24 g, 1.3 mmol) and thionyl chloride (5 mL) was warmed to reflux and was allowed to stir for 2 hours. The mixture was cooled to ambient temperature, concentrated under reduced pressure and diluted with 10 mL toluene. The reaction mixture was again concentrated under reduced pressure and was again diluted with 10 mL toluene. This concentration and dilution was repeated and the crude product was used without further purification.

Workup

  1. temperaturewas warmed
  2. temperatureto reflux
  3. concentrationconcentrated under reduced pressure
  4. additiondiluted with 10 mL toluene
  5. concentrationThe reaction mixture was again concentrated under reduced pressure
  6. additionwas again diluted with 10 mL toluene
  7. concentrationThis concentration and dilution
  8. customthe crude product was used without further purification

Sources & evidence

ORD record
ord-fa7295432e3946d0a44abe78ac1c5234
Source dataset
uspto-grants-2013_07
Patent number
US08492371B2

Reaction notes

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