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

HRID 1244100Notes

Reaction equation

HRID 1244100 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.O>CN(C=O)C>[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 4

HCID 962WaterHCID 74694'-HydroxyacetophenoneHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 13.6 g (100.0 mmol) of 4-hydroxyacetophenone in 100 mL of DMF was added 20 g (144 mmol) of K2CO3, then 12 mL (101 mmol) of benzyl bromide. The reaction was stirred for 1.5 h at ambient temperature, then poured into 300 mL of H2O to give a white precipitate. This was filtered and washed with 50 mL of H2O. The product was taken up in 100 mL of CH2Cl2, and the H2O that separated was drained. The organic layer was extracted with H2O (1×25 mL) and brine (1×25 mL), dried over MgSO4, filtered, and concentrated to 22.1 g (98%) of a white solid as the titled compound. MS (ESI) m/e 226.9, (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 2.50 (m, 3H) 5.21 (s, 2H) 7.11 (m, 2H) 7.41 (m, 5H) 7.92 (m, 2H).

Workup

  1. customto give a white precipitate
  2. filtrationThis was filtered
  3. washwashed with 50 mL of H2O
  4. customthe H2O that separated
  5. extractionThe organic layer was extracted with H2O (1×25 mL) and brine (1×25 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated to 22.1 g (98%) of a white solid as the titled compound

Sources & evidence

ORD record
ord-13cb0b4460944b308d8757e8288ad0fe
Source dataset
uspto-grants-2006_10
Patent number
US07119205B2

Reaction notes

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