Water → 2-chloro-6-phenoxybenzaldehyde

HRID 1956592Notes

Reaction equation

HRID 1956592 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6](F)[C:3]=1[CH:4]=[O:5].[C:11]1([OH:17])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+].O>CC(N(C)C)=O>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:17][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:3]=1[CH:4]=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 996PhenolHCID 11430Potassium CarbonateHCID 678472-Chloro-6-fluorobenzaldehyde

Product 1

HCID 186636022-chloro-6-phenoxybenzaldehydeYield 83.6%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A mixture of 15.8 g (100 mmol) of 2-chloro-6-fluorobenzaldehyde, 9.4 g (100 mmol) of phenol and 20.7 g (150 mmol) of potassium carbonate in 150 ml of dimethylacetamide is heated under reflux for 4 hours. The mixture is allowed to cool, water is added and the mixture is extracted 3× with tert-butyl methyl ether. The organic phases are washed with 2N sodium hydroxide solution and brine, dried over sodium sulfate and concentrated. Bulb tube distillation (175° C., 0.04 mbar) yields 19.46 g (83.64 mmol)=83.6% of 2-chloro-6-phenoxy-benzaldehyde in the form of a yellow oil; 1H-NMR (CDCl3, 200 MHz): 6.75-7.45 (m, 8H); 10.58 (s, 1H).

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 4 hours
  3. temperatureto cool
  4. extractionthe mixture is extracted 3× with tert-butyl methyl ether
  5. washThe organic phases are washed with 2N sodium hydroxide solution and brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. distillationBulb tube distillation (175° C., 0.04 mbar)

Sources & evidence

ORD record
ord-6147f8466c2540c6a618d7bf44609f38
Source dataset
uspto-grants-1998_07
Patent number
US05780501

Reaction notes

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