Water → 4-(3,5-Dichlorophenoxy)benzaldehyde

HRID 1515094Notes

Reaction equation

HRID 1515094 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([Cl:8])[CH:7]=1.F[C:11]1[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CC(N(C)C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([Cl:8])[CH:7]=1)[O:9][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 115713,5-DichlorophenolHCID 680234-Fluorobenzaldehyde

Product 1

HCID 162440874-(3,5-Dichlorophenoxy)benzaldehydeYield 370.3%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
150 °C

Procedure

3,5-Dichlorophenol (500 mg, 3.07 mmol) was dissolved in dimethylacetamide (8.0 mL), and 4-fluorobenzaldehyde (0.390 mL, 0.368 mmol) and cesium carbonate (1.50 g, 3.69 mmol) were sequentially added thereto at room temperature, and then, the resulting mixture was stirred under a nitrogen atmosphere at 150° C. for 3 hours. After the temperature of the reaction solution was returned to room temperature, water was added thereto, and the organic matter was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of ammonium chloride and a saturated sodium chloride solution, then dried over anhydrous sodium sulfate and filtered. Then, the solvent was distilled off under reduced pressure, whereby a crude product was obtained. This crude product was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 85:15 (v/v)), whereby the objective title compound was obtained as a white solid (364 mg, yield: 44%).

Workup

  1. customwas returned to room temperature
  2. extractionthe organic matter was extracted with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous solution of ammonium chloride
  4. dry with materiala saturated sodium chloride solution, then dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. distillationThen, the solvent was distilled off under reduced pressure, whereby a crude product
  7. customwas obtained
  8. customThis crude product was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 85:15 (v/v)), whereby the objective title compound

Sources & evidence

ORD record
ord-4fac7756d7404b54bb1ac3aa97bbc934
Source dataset
uspto-grants-2012_07
Patent number
US08222281B2

Reaction notes

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