Sulfuric Acid → 2-(Methoxycarbonyl)-6-nitrobenzoic acid

HRID 1831011Notes

Reaction equation

HRID 1831011 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]=1[C:13]([OH:15])=[O:14])([O-:3])=[O:2].[CH:16](OC)(OC)OC.S(=O)(=O)(O)O>CO>[C:13]([C:5]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([O:9][CH3:16])=[O:8])([OH:15])=[O:14]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 9005Trimethyl orthoformateHCID 690433-Nitrophthalic acid

Product 1

HCID 43994772-(Methoxycarbonyl)-6-nitrobenzoic acidYield 94.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
62 °C

Procedure

3-Nitrophthalic acid [NPA] (660 kg), trimethyl orthoformate (400 kg), concentrated sulfuric acid (115 kg) and methanol (1180 kg) were mixed, and the mixture was stirred with heating (59 to 65° C.) for about 15 to 20 hours under reflux. The reaction solution was cooled, and concentrated at 40° C. or lower under reduced pressure. The residue was cooled to 30° C. or lower, water (900 L) was added, and the mixture was cooled to 5° C. or lower. The precipitated crystals were separated by a centrifuge, washed with water, and dried at 50° C. for about 50 hours to give methyl 2-carboxy-3-nitrobenzoate [MNA] (666.8 kg, 94.7%).

Workup

  1. temperatureunder reflux
  2. temperatureThe reaction solution was cooled
  3. concentrationconcentrated at 40° C. or lower under reduced pressure
  4. temperatureThe residue was cooled to 30° C.
  5. additionlower, water (900 L) was added
  6. temperaturethe mixture was cooled to 5° C.
  7. customThe precipitated crystals were separated by a centrifuge
  8. washwashed with water
  9. customdried at 50° C. for about 50 hours

Sources & evidence

ORD record
ord-d19cf515b21245c69a4c07b3ba8fb5f7
Source dataset
uspto-grants-2006_06
Patent number
US07067546B2

Reaction notes

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