Phenol → 1-(2,4-Dimethoxyphenyl)-2-phenoxyethan-1-one

HRID 454789Notes

Reaction equation

HRID 454789 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:6]=1[O:13][CH3:14])=[O:4].[C:15]1([OH:21])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+]>CC(=O)CC.CCOC(C)=O>[O:21]([CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:6]=1[O:13][CH3:14])=[O:4])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 986832-Bromo-1-(2,4-dimethoxyphenyl)ethanone

Product 1

HCID 7973791-(2,4-Dimethoxyphenyl)-2-phenoxyethan-1-oneYield 84.6%

Reagents, catalysts & solvents 2

HCID 6569Methyl Ethyl KetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-bromo-2′,4′-dimethoxyacetophenone (5 g, 19.1 mmols) in 25 mL of 2-butanone was added to a suspension of phenol (1.8 g, 19.1 mmols), K2CO3 (2.6 g, 19.1 mmols) and KI (41.5 mg, 0.25 mmols) in 20.0 mL of the same solvent. The solution was then refluxed for 20 hours. The mixture was filtered and the solvent was evaporated off under vacuum. The residue obtained was dissolved in EtOAc and washed with a 10% aqueous solution of NaOH and then with water. The organic extract was dried over Na2SO4, filtered and evaporated under vacuum. Finally, the crude residue was washed with Et2O and dried under low pressure to provide 4.4 g (yield: 84%) of the title compound.

Workup

  1. temperatureThe solution was then refluxed for 20 hours
  2. filtrationThe mixture was filtered
  3. customthe solvent was evaporated off under vacuum
  4. customThe residue obtained
  5. washwashed with a 10% aqueous solution of NaOH
  6. extractionThe organic extract
  7. dry with materialwas dried over Na2SO4
  8. filtrationfiltered
  9. customevaporated under vacuum
  10. washFinally, the crude residue was washed with Et2O
  11. customdried under low pressure

Sources & evidence

ORD record
ord-6efa0d0c99f54fd6af49dd0289d96332
Source dataset
uspto-grants-2013_07
Patent number
US08496975B2

Reaction notes

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