Benzyl Bromide → 2-(Benzyloxy)-1-phenylethan-1-one

HRID 2218242Notes

Reaction equation

HRID 2218242 reaction equation
O[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:10])[CH3:9].[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])([O-])=[O:20].[K+].[K+]>CC(C)=O.CCOC(C)=O.O>[CH2:11]([O:20][CH2:9][C:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:2]=1)=[O:10])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 3

HCID 7498Benzyl BromideHCID 83752'-HydroxyacetophenoneHCID 11430Potassium Carbonate

Product 1

HCID 112531252-(Benzyloxy)-1-phenylethan-1-one

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2′-hydroxyacetophenone (68.1 g, 0.500 mol), benzylbromide (65.4 ml, 94.1 g, 0.550 mol) and K2CO3 (103 g, 0.750 mol) in acetone (1.00L) was stirred and heated to reflux overnight. The resulting mixture was concentrated under reduced pressure to obtain a residue. The obtained residue was dissolved in the mixture of AcOEt and water and then extracted with AcOEt. The extract was washed with brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to give a crude material. The crude material was purified by distillation under reduced pressure to give starting compound 1A as a colorless oil (100 g, yield 88%).

Workup

  1. temperatureheated
  2. temperatureto reflux overnight
  3. concentrationThe resulting mixture was concentrated under reduced pressure
  4. customto obtain a residue
  5. extractionextracted with AcOEt
  6. washThe extract was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0e656a211d7640e0ba2110eee831c511
Source dataset
uspto-grants-2008_08
Patent number
US07410986B2

Reaction notes

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