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

HRID 860936Notes

Reaction equation

HRID 860936 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]([O-])([O-])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 690433-Nitrophthalic acidHCID 53629101Methylorthoformate

Product 1

HCID 43994772-(Methoxycarbonyl)-6-nitrobenzoic acidYield 82.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 3-nitrophthalic acid (211 g) and methyl orthoformate (127 g) in methanol (420 ml) was added conc. sulfuric acid (20 ml) dropwise with stirring. The reaction mixture was heated under reflux for 18 hours and concentrated to dryness. After addition of water (30 ml) to the residue, the mixture was stirred at 3–10° C. for one hour. The precipitated crystals were recrystallized from ethyl acetate-hexane to give pale yellow prisms (185 g, 82%), m.p. 166–168° C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 18 hours
  3. concentrationconcentrated to dryness
  4. additionAfter addition of water (30 ml) to the residue
  5. stirringthe mixture was stirred at 3–10° C. for one hour
  6. customThe precipitated crystals were recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-e044547ed82c47b7a577b733e0a84d69
Source dataset
uspto-grants-2006_12
Patent number
US07153972B2

Reaction notes

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