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

HRID 973393Notes

Reaction equation

HRID 973393 reaction equation
[CH3:1][C:2]([C:4]1[CH:5]=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1)=[O:3].[CH2:11](Cl)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][CH:5]=1)=[O:3]

Participants

5

Reactant 3

HCID 74694'-HydroxyacetophenoneHCID 7503Benzyl ChlorideHCID 11430Potassium Carbonate

Product 1

HCID 2452261-[4-(Benzyloxy)phenyl]ethan-1-oneYield 85.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

27.2 g of 4-hydroxyacetophenone is mixed with 100 ml of dimethylformamide, 25.3 g of benzyl chloride and 30.4 g of potassium carbonate. The resulting mixture is stirred in a stream of nitrogen at 100°-110° C. for 3 hours and then cooled. The cooled mixture is added to about 2 l of ice water to deposit solid. The solid is separated therefrom by filtration and then washed with water until the solid becomes neutral. The washed solid is dried and then recrystallized from 500 ml of ethanol to obtain 38.8 g of 4-benzyloxyacetophenone. Thus obtained 4-benzyloxyacetophenone has a melting point of 92.5°-93° C.

Workup

  1. temperaturecooled
  2. customThe solid is separated
  3. filtrationby filtration
  4. washwashed with water until the solid
  5. customThe washed solid is dried
  6. customrecrystallized from 500 ml of ethanol

Sources & evidence

ORD record
ord-5e6b71504d3f4adaa87d39c908de9f06
Source dataset
uspto-grants-1991_11
Patent number
US05063197

Reaction notes

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