Dimethyl Sulfate → Methyl 5-chloro-2-nitrobenzoate

HRID 570904Notes

Reaction equation

HRID 570904 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([N+:17]([O-:19])=[O:18])=[C:12]([CH:16]=1)[C:13]([OH:15])=[O:14].S(OC)(OC)(=O)=O>CC(C)=O>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([N+:17]([O-:19])=[O:18])=[C:12]([CH:16]=1)[C:13]([O:15][CH3:1])=[O:14]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 172865-Chloro-2-nitrobenzoic acid

Product 1

HCID 171018Methyl 5-chloro-2-nitrobenzoateYield 99.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Potassium carbonate (515 gm) was added to a solution of 5-chloro-2-nitro benzoic acid (500 gm) in acetone (2750 ml) at room temperature. Dimethyl sulphate (306.5 gm) was added to the reaction mixture slowly and heated to reflux for 30 minutes. The reaction mass was filtered and then concentrated to obtain a residual mass. The residual mass was poured to the ice water and extracted with methylene chloride. The solvent was distilled off under reduced pressure to obtain a residual solid of methyl 5-chloro-2-nitrobenzoate (534 gm).

Workup

  1. temperatureheated
  2. temperatureto reflux for 30 minutes
  3. filtrationThe reaction mass was filtered
  4. concentrationconcentrated
  5. customto obtain a residual mass
  6. extractionextracted with methylene chloride
  7. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-e4574b5e32994594880ba1188b1fd87f
Source dataset
uspto-grants-2015_05
Patent number
US09024015B2

Reaction notes

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