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

HRID 65211Notes

Reaction equation

HRID 65211 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:9][C:10]([C:12]1[CH:13]=[CH:14][C:15]([OH:18])=[CH:16][CH:17]=1)=[O:11].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:1]([O:18][C:15]1[CH:16]=[CH:17][C:12]([C:10](=[O:11])[CH3:9])=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 74694'-HydroxyacetophenoneHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 2452261-[4-(Benzyloxy)phenyl]ethan-1-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 17.1 g of benzyl bromide, 13.6 g of 4-hydroxyacetophenone, 27.6 g of potassium carbonate and 200 ml of acetone was refluxed for 7 hours, then cooled and filtered. The filtrate was concentrated, then distilled on a Kugelrohr at 130°-140° C., 0.1 mm Hg. The oil was dissolved in acetone and then concentrated, giving the desired intermediate as a white solid, mp 92°-93° C.

Workup

  1. temperaturewas refluxed for 7 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. distillationdistilled on a Kugelrohr at 130°-140° C.
  6. dissolutionThe oil was dissolved in acetone
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-275f2d6a8d704430a37729bfcf089bc6
Source dataset
uspto-grants-1986_09
Patent number
US04613611

Reaction notes

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