Dimethylformamide → Methyl 2-methoxy-5-methylbenzoate

HRID 1684972

Reaction equation

HRID 1684972 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-613ae75cdef8470297752cd83c854a83
Source dataset
uspto-grants-2012_04
Patent number
US08148371B2

Linked notes

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