Hydrochloric Acid → Methyl 2,4-dimethoxy-5-nitrobenzoate

HRID 2293533Notes

Reaction equation

HRID 2293533 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([N+:14]([O-:16])=[O:15])=[CH:8][C:4]=1[C:5]([OH:7])=[O:6].[C:17](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O.Cl>CC(=O)CC>[CH3:1][O:2][C:3]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([N+:14]([O-:16])=[O:15])=[CH:8][C:4]=1[C:5]([O:7][CH3:17])=[O:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 133076602,4-Dimethoxy-5-nitrobenzoic acid

Product 1

HCID 11622839Methyl 2,4-dimethoxy-5-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A 7.00 g portion of 2,4-dimethoxy-5-nitrobenzoic acid was dissolved in 2-butanone, and 9.90 g of potassium carbonate and 3.6 ml of dimethyl sulfate were added, followed by 3 hours of heating under reflux. After completion of the reaction, the reaction solution was poured into 1N hydrochloric acid aqueous solution, and the thus precipitated product of interest was collected by filtration, washed with water and then dried under a reduced pressure to give 5.45 g of methyl 2,4-dimethoxy-5-nitrobenzoate.

Workup

  1. temperatureof heating
  2. temperatureunder reflux
  3. customAfter completion of the reaction
  4. filtrationthe thus precipitated product of interest was collected by filtration
  5. washwashed with water
  6. customdried under a reduced pressure

Sources & evidence

ORD record
ord-5fe48746079b490ebf1d5cd39b45ae66
Source dataset
uspto-grants-1997_11
Patent number
US05686482

Reaction notes

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