Acetyl chloride → 2-(Methoxycarbonyl)-6-nitrobenzoic acid

HRID 2060865Notes

Reaction equation

HRID 2060865 reaction equation
[C:1](Cl)(=O)C.[N+:5]([C:8]1[CH:16]=[CH:15][CH:14]=[C:10]([C:11]([OH:13])=[O:12])[C:9]=1[C:17]([OH:19])=[O:18])([O-:7])=[O:6]>CO>[CH3:1][O:12][C:11](=[O:13])[C:10]1[C:9](=[C:8]([N+:5]([O-:7])=[O:6])[CH:16]=[CH:15][CH:14]=1)[C:17]([OH:19])=[O:18]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 690433-Nitrophthalic acid

Product 1

HCID 43994772-(Methoxycarbonyl)-6-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To MeOH (100 ml) at 0° C. was added acetyl chloride (14.5 mL, 203.4 mmol) and the solution stirred at rt for 1 h. 3-Nitrophthalic acid (25.7 g, 121.7 mmol) was added and the mixture heated at reflux for 22 h. The reaction was cooled to rt and partitioned between water (80 mL) and EtOAc (3×80 mL). The combined organic phase was dried (MgSO4) and solvent removed in vacuo to give the title compound: Data in agreement with previous reports (Roger, M. E.; Averill, B. A. J. Org. Chem. 1986, 51, 3308-3314).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 22 h
  3. temperatureThe reaction was cooled to rt
  4. custompartitioned between water (80 mL) and EtOAc (3×80 mL)
  5. dry with materialThe combined organic phase was dried (MgSO4) and solvent
  6. customremoved in vacuo

Sources & evidence

ORD record
ord-2089e3645e204b0796a5977fa015ce86
Source dataset
uspto-grants-2012_10
Patent number
US08278442B2

Reaction notes

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