Hydrochloric Acid → 3-(Methoxycarbonyl)benzoic acid

HRID 617664Notes

Reaction equation

HRID 617664 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([O:13]C)=[O:12])[CH:6]=1)=[O:4].CN(C)N.Cl>O>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH:8]=[CH:9][CH:10]=1)[C:11]([OH:13])=[O:12])=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 59761,1-DimethylhydrazineHCID 15088Dimethyl isophthalate

Product 1

HCID 6018803-(Methoxycarbonyl)benzoic acidYield 24.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of dimethyl m-phthalate (40.0 g, 0.206 mol) and 1,1-dimethylhydrazine (78.3 mL, 1.03 mol) was stirred at room temperature for 17 h and refluxed under heating for 21 h. The reaction mixture was concentrated, and the residue was washed with dichloromethane to give a powder, to which were added water (300 mL) and 1N hydrochloric acid (300 mL). The precipitated solids were collected by filtration, dried under reduced pressure, and recrystallized from chloroformmethanol (9:1) to give 9.05 g (24%) of 3-methoxycarbonylbenzoic acid as colorless crystals.

Workup

  1. temperaturerefluxed
  2. temperatureunder heating for 21 h
  3. concentrationThe reaction mixture was concentrated
  4. washthe residue was washed with dichloromethane
  5. customto give a powder
  6. filtrationThe precipitated solids were collected by filtration
  7. customdried under reduced pressure
  8. customrecrystallized from chloroformmethanol (9:1)

Sources & evidence

ORD record
ord-59b2edbe86654d3baa61e779bf6eba10
Source dataset
uspto-grants-1999_09
Patent number
US05948785

Reaction notes

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