Hydrochloric Acid → Methyl 3-(chlorocarbonyl)-5-nitrobenzoate

HRID 1261181Notes

Reaction equation

HRID 1261181 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[C:6]([C:7](O)=[O:8])[CH:5]=1.[ClH:17]>S(Cl)(Cl)=O>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[C:6]([C:7]([Cl:17])=[O:8])[CH:5]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 747761,3-Benzenedicarboxylic acid, 5-nitro-, 1-methyl ester

Product 1

HCID 74774Methyl 3-(chlorocarbonyl)-5-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

A suspension of 5-nitro-isophthalic acid mono methyl ester (22.52 g, 100.0 mmol) in thionyl chloride (50 ml) was heated to reflux for 6 hours (until the production of SO2 and HCl-gas ceased). The excess of thionyl chloride was removed under reduced pressure, the residue was dissolved in DCM and the product was precipitated by addition of hexane to give a white solid. Yield: 24.10 g (99%).

Workup

  1. temperaturewas heated
  2. customThe excess of thionyl chloride was removed under reduced pressure
  3. dissolutionthe residue was dissolved in DCM
  4. customthe product was precipitated by addition of hexane
  5. customto give a white solid

Sources & evidence

ORD record
ord-0fba3e45dacc44129240e3da748448cb
Source dataset
uspto-grants-2013_06
Patent number
US08470860B2

Reaction notes

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