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

HRID 30231

Reaction equation

HRID 30231 reaction equation
[CH3:1][C:2]([C:4]1[CH:5]=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1)=[O:3].C(=O)([O-])[O-].[K+].[K+].[F:17][C:18]([F:29])([F:28])[O:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Br)=[CH:22][CH:21]=1>CC(C)=O>[F:17][C:18]([F:28])([F:29])[O:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][O:10][C:7]2[CH:8]=[CH:9][C:4]([C:2](=[O:3])[CH3:1])=[CH:5][CH:6]=2)=[CH:22][CH:21]=1

Participants

5

Reactant 3

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

Product 1

HCID 525612731-[4-(4-Trifluoromethoxybenzyloxy)phenyl]ethanoneYield 80.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of 300.0 mg (2.203 mmol) 4-hydroxyacetophenone and 305 mg (2.207 mmol) potassium carbonate in 15 ml acetone was added 868.7 mg (3.304 mmol) 4-(trifluoromethoxy)benzylbromide dropwise and heated under reflux for 1 d. The solvent was evaporated and to the residue was added ethyl acetate. The organic phase was washed with 1M aqueous HCl solution and water, dried over magnesium sulfate. The solvent was evaporated and the residue was subjected to silica gel chromatography (ethyl acetate/n-heptane 1:2) to yield 552 mg (1.779 mmol) 1-[4-(4-trifluoromethoxy-benzyloxy)-phenyl]-ethanone.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1 d
  3. customThe solvent was evaporated and to the residue
  4. additionwas added ethyl acetate
  5. washThe organic phase was washed with 1M aqueous HCl solution and water
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was evaporated

Sources & evidence

ORD record
ord-efd148e6c9f346ae90a7dbd83987925f
Source dataset
uspto-grants-2008_09
Patent number
US07423060B2

Linked notes

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