4'-Hydroxyacetophenone → 1-[4-(Benzyloxy)phenyl]ethan-1-one

HRID 446807Notes

Reaction equation

HRID 446807 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:17](Cl)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C=O)C>[CH2:17]([O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 74694'-HydroxyacetophenoneHCID 7503Benzyl ChlorideHCID 11430Potassium Carbonate

Product 1

HCID 2452261-[4-(Benzyloxy)phenyl]ethan-1-oneYield 81,208.102%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(4-hydroxyphenyl)ethanone (10 g, 0.07 mol) in DMF (15 mL), were added anhydrous K2CO3 (20.3 g, 0.14 mol) and benzyl chloride (11.16 g, 0.08 mmol). The reaction mixture was then stirred at RT for 16 h, quenched with ice, and a solid was precipitated. The obtained solid residue was filtered and dried in vacuo to afford 1-(4-(benzyloxy)phenyl)ethanone (14.7 g, 89%) as a solid.

Workup

  1. customquenched with ice
  2. customa solid was precipitated
  3. filtrationThe obtained solid residue was filtered
  4. customdried in vacuo

Sources & evidence

ORD record
ord-480fad6ad258459cb20db22c052f6e95
Source dataset
uspto-grants-2013_07
Patent number
US08481534B2

Reaction notes

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