Thionyl Chloride → 5-Chloro-2-methoxybenzoyl chloride

HRID 538764Notes

Reaction equation

HRID 538764 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].O=S(Cl)[Cl:15]>>[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 the 5-chloro-2-methoxybenzoic acid (0.94 g, 5.0 mmol) and SOCl2 (10 mL) was warmed to reflux and was allowed to stir for 2 h. The mixture was cooled to ambient temperature, concentrated under reduced pressure and diluted with 10 mL toluene. This material was again concentrated under reduced pressure and was again diluted with 10 mL toluene. This concentration and dilution was repeated for an addition time and the crude material was carried on without further purification or characterization.

Workup

  1. temperaturewas warmed
  2. temperatureto reflux
  3. concentrationconcentrated under reduced pressure
  4. additiondiluted with 10 mL toluene
  5. concentrationThis material was again concentrated under reduced pressure
  6. additionwas again diluted with 10 mL toluene
  7. concentrationThis concentration and dilution
  8. customthe crude material was carried on without further purification or characterization

Sources & evidence

ORD record
ord-f3d2c4f3fe1f4bb1b885cb434dcc9921
Source dataset
uspto-grants-2014_10
Patent number
US08865753B2

Reaction notes

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