Dimethylformamide → 3-Chloro-2-methoxybenzoic acid methyl ester

HRID 430463Notes

Reaction equation

HRID 430463 reaction equation
[CH3:1]I.[Cl:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:6](C(O)=O)[C:5]=1O.[C:14](=[O:17])([O-])[O-:15].[K+].[K+].CN(C)[CH:22]=[O:23]>O>[CH3:1][O:15][C:14](=[O:17])[C:6]1[CH:10]=[CH:11][CH:12]=[C:4]([Cl:3])[C:5]=1[O:23][CH3:22]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 745853-Chlorosalicylic acid

Product 1

HCID 148770593-Chloro-2-methoxybenzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

8.2 ml of methyl iodide is added to 10 g of 3-chlorosalicylic acid and 18 g of potassium carbonate in 88 ml of dimethylformamide, and the mixture is stirred overnight. It is diluted with water, extracted with ethyl acetate, the organic phase is dried (Na2SO4) and concentrated by evaporation. The residue is distilled on a bulb tube. 10 g of 3-chloro-2-methoxybenzoic acid methyl ester is obtained, boiling point 100° C./0.17 mbar.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialthe organic phase is dried (Na2SO4)
  3. concentrationconcentrated by evaporation
  4. distillationThe residue is distilled on a bulb tube

Sources & evidence

ORD record
ord-1c14ccc5da3b40e5b8542e9ba683e3c0
Source dataset
uspto-grants-2001_11
Patent number
US06323199B1

Reaction notes

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