Dimethylformamide → Methyl 3-chloro-2-methylbenzoate

HRID 446025Notes

Reaction equation

HRID 446025 reaction equation
IC.[Cl:3][C:4]1[C:5]([CH3:13])=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=[O:8].[C:14](=O)([O-])[O-].[K+].[K+].CN(C)C=O>C(OCC)(=O)C.O>[Cl:3][C:4]1[C:5]([CH3:13])=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([O:9][CH3:14])=[O:8]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 820103-Chloro-2-methylbenzoic acid

Product 1

HCID 5077673Methyl 3-chloro-2-methylbenzoateYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Iodomethane (1.96 ml, 31.5 mmol) was added to a mixture of 3-chloro-2-methylbenzoic acid (3.58 g, 21 mmol), potassium carbonate (5.8 g, 42 mmol) and N,N-dimethylformamide (35.9 ml), followed by stirring at mom temperature for 18 hours and 30 minutes. Water and ethyl acetate were added to the reaction liquid, and the organic layer was extracted. The organic layer was sequentially washed with a saturated aqueous ammonium chloride solution and brine, and then dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography (elution solvent: heptane/ethyl acetate) to give the title compound (3.67 g, yield: 97%).

Workup

  1. extractionthe organic layer was extracted
  2. washThe organic layer was sequentially washed with a saturated aqueous ammonium chloride solution and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (elution solvent: heptane/ethyl acetate)

Sources & evidence

ORD record
ord-5e4e27c283f045258e349207b267ec1c
Source dataset
uspto-grants-2013_07
Patent number
US08476301B2

Reaction notes

Loading…