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

HRID 612776Notes

Reaction equation

HRID 612776 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

Sources & evidence

ORD record
ord-0ed202264fe34dbb8b06ac1b192f7f7f
Source dataset
uspto-grants-1999_12
Patent number
US06004989

Reaction notes

Loading…