Dimethylformamide → Methyl 2-methoxy-5-methylbenzoate

HRID 2354837Notes

Reaction equation

HRID 2354837 reaction equation
[CH3:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=O)[C:5]([OH:11])=[CH:4][CH:3]=1.[C:12](=O)([O-])[O-].[K+].[K+].IC.CN([CH:23]=[O:24])C>>[CH3:12][O:11][C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:10][C:6]=1[C:7]([O:24][CH3:23])=[O:9]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 69735-Methylsalicylic acidHCID 11430Potassium Carbonate

Product 1

HCID 10241396Methyl 2-methoxy-5-methylbenzoateYield 95%

Procedure

To 5-methylsalicylic acid (3.04 g, 20 mmol) in DMF (100 ml) were added potassium carbonate (8.28 g, 60 mmol) and iodomethane (6.24 g, 44 mmol) under ice cooling and then the mixture was stirred at room temperature for 12 hours. The mixture were extracted by adding 5% sodium hydrogensulfite and ethyl acetate, and the extracted organic layer was washed with 5% citric acid and 5% brine. The organic layer was dried over anhydrous magnesium sulfate and concentrated. The residue was purified by column chromatography (hexane-ethyl acetate) to give the captioned compound (3.43 g, 19.1 mmol, yield: 95%) as a colorless oil.

Workup

  1. extractionThe mixture were extracted
  2. additionby adding 5% sodium hydrogensulfite and ethyl acetate
  3. washthe extracted organic layer was washed with 5% citric acid and 5% brine
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-cb41b36183e84a70850cff7b768c8127
Source dataset
uspto-grants-2010_07
Patent number
US07754728B2

Reaction notes

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