Water → p-Benzyloxypropiophenone

HRID 351231Notes

Reaction equation

HRID 351231 reaction equation
[CH3:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)=[O:4].[CH2:12](Cl)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+].O>CCO>[CH2:12]([O:11][C:8]1[CH:7]=[CH:6][C:5]([C:3](=[O:4])[CH2:2][CH3:1])=[CH:10][CH:9]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 62714'-HydroxypropiophenoneHCID 7503Benzyl ChlorideHCID 11430Potassium Carbonate

Product 1

HCID 78246p-BenzyloxypropiophenoneYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-hydroxypropiophenone (20 g), benzyl chloride (16.1 ml), K2CO3 (12.9 g) and KI (2.21 g) in EtOH (80 ml) and H2O (1 ml) was stirred under reflux condition for 4 hours. The reaction mixture was cooled and filtered. Appeared crystal was dissovled with EtOAc and water. Organic layer was separated and washed with water and brine, dried over MgSO4 and filtered. Filtrate was evaporated under reduced pressure to give 30.0 g (94%) of 1-[4-(benzyloxy)phenyl]-1-propanone as a crystal.

Workup

  1. temperatureunder reflux condition for 4 hours
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered
  4. customOrganic layer was separated
  5. washwashed with water and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customFiltrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-abe8f3bb87514c698f6e0c5a83e448ce
Source dataset
uspto-grants-2007_02
Patent number
US07183306B2

Reaction notes

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