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

HRID 1977387Notes

Reaction equation

HRID 1977387 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-66ee8325b1b242e39fc99b6a0fd55e88
Source dataset
uspto-grants-2001_05
Patent number
US06232334B1

Reaction notes

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