Water → HCID 67429060, compound

HRID 878777Notes

Reaction equation

HRID 878777 reaction equation
[C:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][C:5]=1[Cl:13])(=[O:3])[CH3:2].[C:14](=O)([O-])[O-].[K+].[K+].IC.O>CN(C)C=O>[C:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([O:10][CH3:14])=[O:9])=[CH:6][C:5]=1[Cl:13])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 697171834-Acetyl-3-chlorobenzoic acid

Product 1

HCID 67429060HCID 67429060, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-acetyl-3-chlorobenzoic acid (synthesized by the method of Tetrahedron 1988, 44, 1631, 700 mg, 3.52 mmol) in N,N-dimethylformamide (4 mL) were added potassium carbonate (974 mg, 7.05 mmol) and iodomethane (658 μL, 10.57 mmol) at room temperature, and the mixture was stirred at room temperature for 1 hour. To the reaction solution was added water, and the mixture was extracted with ethyl acetate three times. The organic layer was combined, filtered through Phase-separator (Varian Inc.), and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0→75:25) to give methyl 4-acetyl-3-chlorobenzoate (707 mg, 94%) as a pale yellow powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate three times
  2. filtrationfiltered through Phase-separator (Varian Inc.)
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0→75:25)

Sources & evidence

ORD record
ord-fd08836e4dad4c5bb3dd54a05dcb0aba
Source dataset
uspto-grants-2015_03
Patent number
US08987445B2

Reaction notes

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