Water → 4-(4-Fluorophenoxy)benzaldehyde

HRID 1275130Notes

Reaction equation

HRID 1275130 reaction equation
[F: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>[F: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 97324-FluorophenolHCID 11430Potassium CarbonateHCID 680234-Fluorobenzaldehyde

Product 1

HCID 38568024-(4-Fluorophenoxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A solution of 4-fluorophenol (4.52 g, 40.29 mmol), 4-fluorobenzaldehyde (5.00 g, 40.29 mmol) and potassium carbonate (6.70 g, 48.35 mmol) in DMAC (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 the title compound.

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-ff426b0cfa164d4786b150ea0897344a
Source dataset
uspto-grants-2000_12
Patent number
US06160000

Reaction notes

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