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

HRID 922322Notes

Reaction equation

HRID 922322 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>C(#N)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

6

Reactant 3

HCID 74694'-HydroxyacetophenoneHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 2452261-[4-(Benzyloxy)phenyl]ethan-1-oneYield 85.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a stirring solution of 1-(4-hydroxyphenyl)ethanone (5 g, 36 mmol) in Acetonitrile 50 mL was added potassium carbonate (9.9 g, 72 mmol) and benzyl bromide (7.5 g, 44 mmol) and stirred at RT for overnight, reaction mass was diluted with water and extracted with ethyl acetate, organic layer was given water and brine washes, dried over Na2SO4, evaporation under reduced pressure yields titled compound as white solid (7 g Yield: 84.1%): 1H NMR (300 MHz, CDCl3): δ 7.85-7.88 (d, 2H), 7.25-7.37 (m, 5H), 6.92-6.95 (d, 2H), 5.06 (s, 2H), 2.48 (s, 3H).

Workup

  1. customreaction mass
  2. extractionextracted with ethyl acetate, organic layer
  3. dry with materialdried over Na2SO4, evaporation under reduced pressure

Sources & evidence

ORD record
ord-f88a81771f29478cb4ed25912a3f2552
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Reaction notes

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