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

HRID 322931Notes

Reaction equation

HRID 322931 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+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(C(C)=O)C.[I-].[K+]>[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:6][CH:5]=1)=[O:3]

Participants

6

Reactant 3

HCID 74694'-HydroxyacetophenoneHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 2452261-[4-(Benzyloxy)phenyl]ethan-1-oneYield 90.3%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 4-hydroxyacetophenone (30 g), potassium carbonate (33.4 g), potassium iodide (1 g) and benzyl bromide (41.4 g) in methyl ethyl ketone (500 mL) is heated at reflux for 18 hours. The cooled reaction mixture is filtered and the filtrate evaporated. The residue is crystallised from cyclohexane to give 4-benzyloxyacetophenone (45 g, 90%).

Workup

  1. temperatureis heated
  2. temperatureat reflux for 18 hours
  3. customThe cooled reaction mixture
  4. filtrationis filtered
  5. customthe filtrate evaporated
  6. customThe residue is crystallised from cyclohexane

Sources & evidence

ORD record
ord-a73ef722221d471fa9656b8906ca8a09
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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