Water → o-Phenoxybenzaldehyde

HRID 1836684Notes

Reaction equation

HRID 1836684 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.F[C:9]1[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=1[CH:11]=[O:12].C([O-])([O-])=O.[K+].[K+].O>CN(C)C(=O)C>[O:7]([C:9]1[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=1[CH:11]=[O:12])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 996PhenolHCID 11430Potassium CarbonateHCID 67970o-Fluorobenzaldehyde

Product 1

HCID 88060o-Phenoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of phenol (1.8888 g, 0.0201 mol) and 2-fluorobenzaldehyde (2.14 mL, 0.0203 mol) in N,N-dimethylacetamide (20 mL) was added anhydrous K2CO3 (3.0798 g, 0.0223 mol). The resulting heterogenous mixture was refluxed for 3 h. The resulting green mixture was then treated with H2O (100 mL) and extracted with EtOAc (2×100 mL). The combined organic extracts were washed with H2O (4×100 mL), dried over Na2SO4, filtered and concentrated. The resulting dark residue was purified by flash chromatography on silica gel (10% EtOAc in hexane) to yield 2-phenoxybenzaldehyde as a light yellow oil.

Workup

  1. temperatureThe resulting heterogenous mixture was refluxed for 3 h
  2. extractionextracted with EtOAc (2×100 mL)
  3. washThe combined organic extracts were washed with H2O (4×100 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting dark residue was purified by flash chromatography on silica gel (10% EtOAc in hexane)

Sources & evidence

ORD record
ord-afb696f678b14bb988b65beef39cd0a5
Source dataset
uspto-grants-2004_08
Patent number
US06777421B2

Reaction notes

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