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

HRID 2358196Notes

Reaction equation

HRID 2358196 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-isophtalic 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-61f3ad3074984c1a9da5c40da000cbfb
Source dataset
uspto-grants-2010_07
Patent number
US07763642B2

Reaction notes

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