Water → 4-(4-Methylphenoxy)benzaldehyde

HRID 1058642Notes

Reaction equation

HRID 1058642 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH:10]1[C:15]([OH:16])=[CH:14][CH:13]=[C:12]([CH3:17])[CH:11]=1.C(=O)([O-])[O-].[K+].[K+].O>CC(N(C)C)=O>[CH3:17][C:12]1[CH:11]=[CH:10][C:15]([O:16][C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 2879P-CresolHCID 11430Potassium CarbonateHCID 680234-Fluorobenzaldehyde

Product 1

HCID 47392074-(4-Methylphenoxy)benzaldehydeYield 66%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

In an argon atmosphere, 4-fluorobenzaldehyde (0.53 mL, 5.0 mmol) and p-cresol (648 mg, 6.0 mmol) were dissolved in dimethylacetamide (8 mL), and to the solution were added potassium carbonate (828 mg, 6.0 mmol) and cupric oxide (95 mg, 0.50 mmol) and the mixture was heated under reflux for 1.5 hours. The reaction solution was cooled down to room temperature, and water was added, and then the mixture was extracted with ethyl acetate. The organic layer was washed with a 0.5 N aqueous sodium hydroxide solution, water and brine, and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (6:1 hexane/ethyl acetate) to obtain 4-(4methylphenoxy)benzaldehyde (697 mg, 66%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1.5 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with a 0.5 N aqueous sodium hydroxide solution, water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (6:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-57590153509d4755a985db28414f131e
Source dataset
uspto-grants-2003_02
Patent number
US06518268B1

Reaction notes

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