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

HRID 1030454Notes

Reaction equation

HRID 1030454 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](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C)C=O>[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 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 2452261-[4-(Benzyloxy)phenyl]ethan-1-oneYield 83.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4'-Hydroxyacetophenone (40g) and potassium carbonate (60.9 g) were mixed in dimethyl formamide (250 ml). Benzyl bromide (36.7 ml) was added dropwise to the mixture, and the mixture was stirred at room temperature for 1 hour and further at 50° to 60° C. for 1 hour. The reaction mixture was poured into ice-water, and the precipitating crystals were collected by filtration and recrystallized from methanol to give 4'-benzyloxyacetophenone (55.4g, 83.3%). m.p. 93°-94° C.

Workup

  1. filtrationthe precipitating crystals were collected by filtration
  2. customrecrystallized from methanol

Sources & evidence

ORD record
ord-b57a0a450dcf47ae8a9b32e70553b056
Source dataset
uspto-grants-1992_04
Patent number
US05106732

Reaction notes

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