Water → 4-(4-Methylphenoxy)benzaldehyde

HRID 2185038Notes

Reaction equation

HRID 2185038 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.F[C:10]1[CH:17]=[CH:16][C:13]([CH:14]=[O:15])=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+].O>CC(N(C)C)=O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:10]2[CH:17]=[CH:16][C:13]([CH:14]=[O:15])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

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

Product 1

HCID 47392074-(4-Methylphenoxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A solution of 4-methylphenol (4.52 g, 40.29 mmol), 4-fluorobenzaldehyde (5.00 g, 40.29 mmol) and potassium carbonate (6.70 g, 48.35 mmol) in dimethylacetamide (40 mL) was refluxed for 12 h and cooled to room temperature. Water was added and the reaction mixture was extracted with ethyl acetate. The organic extract was washed with brine, dried over sodium sulfate, filtered and concentrated to afford an oil which was chromatographed on silica gel (15% ethyl acetate/hexane) to afford 4-(4′-methylphenoxy)benzaldehyde.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. extractionThe organic extract
  3. washwas washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto afford an oil which
  8. customwas chromatographed on silica gel (15% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-8b59cc173da9488698b4b0c658fe166f
Source dataset
uspto-grants-2002_06
Patent number
US06399640B1

Reaction notes

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