Methanol → Methyl 4-chloro-2-methoxy-5-nitrobenzoate

HRID 1059295Notes

Reaction equation

HRID 1059295 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:14][CH3:15])[C:5](=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:6]([OH:8])=[O:7].S(=O)(=O)(O)O.[CH3:21]O>>[Cl:1][C:2]1[CH:3]=[C:4]([O:14][CH3:15])[C:5](=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:6]([O:8][CH3:21])=[O:7]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 128487494-Chloro-2-methoxy-5-nitrobenzoic acid

Product 1

HCID 18670222Methyl 4-chloro-2-methoxy-5-nitrobenzoate

Procedure

To a solution of 3.1 g of 4-chloro-5-nitro-o-anisic acid in methanol (100 ml) was added a catalytic amount of sulfuric acid and the resulting mixture was heated under reflux for 3 hours. Then the reaction mixture was poured into ice/water and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, 3.3 g of methyl 4-chloro-5-nitro-o-anisate was obtained as pale yellow crystals.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 3 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationAfter distilling off the solvent under reduced pressure

Sources & evidence

ORD record
ord-67639995a53349839fff77166b274da7
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

Loading…