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

HRID 567398Notes

Reaction equation

HRID 567398 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

A mixture of 3-nitrophtalic acid [NPA] (660 kg), trimethyl orthoformate (400 kg), concentrated sulfuric acid (115 kg) and methanol (1180 kg) was stirred under reflux at 59-65° C. for about 15-20 hours. The reaction solution was cooled and concentrated under reduced pressure at not more than 40° C. The residue was cooled to not more than 30° C., to which was added water (900 L), and the solution was cooled to not more than 5° C. The precipitated crystals were centrifuged, 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. temperatureThe reaction solution was cooled
  2. concentrationconcentrated under reduced pressure at not more than 40° C
  3. temperatureThe residue was cooled to not more than 30° C., to which
  4. additionwas added water (900 L)
  5. temperaturethe solution was cooled to not more than 5° C
  6. washwashed with water
  7. customdried at 50° C. for about 50 hours

Sources & evidence

ORD record
ord-3d33ac453de34927979bf3577100cf23
Source dataset
uspto-grants-2001_01
Patent number
US06177587B1

Reaction notes

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