4'-Hydroxyacetophenone → 1-[4-(4-Trifluoromethoxybenzyloxy)phenyl]ethanone

HRID 1678057Notes

Reaction equation

HRID 1678057 reaction equation
[CH3:1][C:2]([C:4]1[CH:5]=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1)=[O:3].[F:11][C:12]([F:23])([F:22])[O:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Br)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.O>[F:11][C:12]([F:22])([F:23])[O:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][O:10][C:7]2[CH:8]=[CH:9][C:4]([C:2](=[O:3])[CH3:1])=[CH:5][CH:6]=2)=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 74694'-HydroxyacetophenoneHCID 11430Potassium CarbonateHCID 1427851-(Bromomethyl)-4-(trifluoromethoxy)benzene

Product 1

HCID 525612731-[4-(4-Trifluoromethoxybenzyloxy)phenyl]ethanoneYield 102.6%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A stirred mixture of 4-hydroxyacetophenone (0.9 g, 6.6 mmol), 4-(trifluoromethoxy)benzyl bromide (2.0 g, 7.8 mmol) and potassium carbonate (1.4 g, 10 mmol) in acetone (25 mL) was heated at reflux for 7 hours. The mixture was then cooled, diluted with H2O (50 mL) and extracted with EtOAc (2×100 mL). The organic portions were combined, washed with brine and dried (Na2SO4). Filtration and removal of solvent in vacuo afforded 2.1 g of a crude yellow semi-solid which was used without further purification.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 7 hours
  3. temperatureThe mixture was then cooled
  4. extractionextracted with EtOAc (2×100 mL)
  5. washwashed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationFiltration and removal of solvent in vacuo

Sources & evidence

ORD record
ord-261677eb93eb4f75b0e271bf7f802dbc
Source dataset
uspto-grants-2011_08
Patent number
US08008487B2

Reaction notes

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