Water → 2-Chloro-4-methoxybenzaldehyde

HRID 7429

Reaction equation

HRID 7429 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[C:11](=O)([O-])[O-].[K+].[K+].CI.O>CN(C)C=O>[Cl:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 1853632-Chloro-4-hydroxybenzaldehyde

Product 1

HCID 93617462-Chloro-4-methoxybenzaldehydeYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-chloro-4-hydroxybenzaldehyde (2 g, 12.8 mmol) in N,N-dimethylformamide (25 mL) were added potassium carbonate (3.46 g, 25 mmol) and methyl iodide (large excess) and the mixture was stirred at room temperature for 18 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 (1.55 g, 70%).

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-0c167f9a9f1b44cc9678a067bdab38e6
Source dataset
uspto-grants-2006_08
Patent number
US07087597B1

Linked notes

Loading…