Thionyl Chloride → 3-methoxy-4-nitro-benzoyl Chloride

HRID 412715Notes

Reaction equation

HRID 412715 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[C:6](O)=[O:7].S(Cl)([Cl:17])=O>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[C:6]([Cl:17])=[O:7]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 787643-Methoxy-4-nitrobenzoic acid

Product 1

HCID 111276553-methoxy-4-nitro-benzoyl ChlorideYield 99.6%

Procedure

A heterogeneous mixture comprising 3-methoxy-4-nitrobenzoic acid (15.42 g, 78.2 mmol) and thionyl chloride (70 mL, 391 mmol) was heated at reflux for one hour. The excess thionyl chloride was removed by distillation and the residue was concentrated in vacuo to provide 3-methoxy-4-nitrobenzoyl chloride (16.8 g, 99% yield) as a light yellow solid; MS (PB-PCI) C8H6CINO4 m/e calc 215.59; found 216 (MH+).

Workup

  1. temperatureat reflux for one hour
  2. customThe excess thionyl chloride was removed by distillation
  3. concentrationthe residue was concentrated in vacuo

Sources & evidence

ORD record
ord-50d3dcfb9f404e18b08f0783afbe21fa
Source dataset
uspto-grants-2003_05
Patent number
US06562854B2

Reaction notes

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