Water → Methyl 3-chloro-p-anisate

HRID 7424

Reaction equation

HRID 7424 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1O)[C:5]([OH:7])=[O:6].[C:12](=O)([O-])[O-].[K+].[K+].CI.O.CN(C)[CH:23]=[O:24]>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:24][CH3:23])[C:5]([O:7][CH3:12])=[O:6]

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 198603-Chloro-4-hydroxybenzoic acid

Product 1

HCID 123469Methyl 3-chloro-p-anisateYield 100%

Conditions

Temperature
60 °C

Procedure

To a solution of 3-chloro-4-hydroxybenzoic acid (3.45 g, 20 mmol) in N,N-dimethylformamide (10 mL) were added potassium carbonate (6.9 g, 50 mmol) and methyl iodide (large excess) and the mixture was stirred at 60° C. for 2 h. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give an almost pure title compound (4.0 g, 100%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-32baeeeecd374a7189596c7a144284aa
Source dataset
uspto-grants-2006_08
Patent number
US07087597B1

Linked notes

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