Dimethylformamide → Methyl 4-chloro-2-methoxybenzoate

HRID 1289755Notes

Reaction equation

HRID 1289755 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6](O)[C:7](=[CH:11][CH:12]=1)[C:8]([OH:10])=[O:9].I[CH3:15].CN(C)[CH:18]=[O:19]>>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:8]([O:10][CH3:15])=[O:9])=[C:11]([O:19][CH3:18])[CH:12]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 787824-Chlorosalicylic acid

Product 1

HCID 327084Methyl 4-chloro-2-methoxybenzoateYield 77.4%

Procedure

To a suspension of 60% sodium hydride oil (3.4 g) in dimethylformamide (25 ml) was added 4-chlorosalicylic acid (7.33 g) under ice-cooling, and the mixture was stirred for 1 hour at room temperature. After the stirring, iodomethane (25 g) was dropwise added to the mixture and the mixture was reacted for 1 hour at 50° C., which was followed by extraction with ether. The extract was washed with water and dried over magnesium sulfate. After the concentration, the residue was chromatographed on silica gel (hexane-ethyl acetate) to give 6.60 g of a colorless transparent liquid (yield 77.4%).

Workup

  1. temperaturecooling
  2. customthe mixture was reacted for 1 hour at 50° C.
  3. extractionwhich was followed by extraction with ether
  4. washThe extract was washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationAfter the concentration
  7. customthe residue was chromatographed on silica gel (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-1f46d65d7b2a45d7b61e8f1cf9a98621
Source dataset
uspto-grants-1998_05
Patent number
US05750545

Reaction notes

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