Benzyl Bromide → 1-(3-(Phenylmethoxy)phenyl)ethan-1-one

HRID 862945Notes

Reaction equation

HRID 862945 reaction equation
[H-].[Na+].[CH3:3][C:4]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]([OH:12])[CH:11]=1)=[O:5].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C=O)C>[CH3:3][C:4]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:11]=1)=[O:5]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 84873-HydroxyacetophenoneHCID 24758Sodium hydride

Product 1

HCID 986891-(3-(Phenylmethoxy)phenyl)ethan-1-oneYield 97.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of sodium hydride (4.5 g of 80% mineral oil dispersion, 0.15 mol), which had been washed free of mineral oil, in DMF (25 ml) was added, dropwise with cooling, a solution of 3-hydroxyacetophenone (20.5 g, 0.15 mol) in DMF (25 ml). Upon completion of the addition, the mixture was allowed to stir at room temperature for 15 min, at which time was added benzyl bromide (25.6 g, 0.15 mol). The resulting mixture was allowed to stir at room temperature overnight, then was partitioned between EtOAc and 3M HCl. The aqueous phase was extracted with EtOAc, and the combined organic extracts were washed successively with 1M NaOH, H2O and saturated aqueous NaCl and dried. The solvent was removed in vacuo to afford the title compound (33 g, 97%), which was used without further purification.

Workup

  1. washhad been washed free of mineral oil, in DMF (25 ml)
  2. additionwas added
  3. temperaturedropwise with cooling
  4. additionUpon completion of the addition
  5. stirringto stir at room temperature overnight
  6. customwas partitioned between EtOAc and 3M HCl
  7. extractionThe aqueous phase was extracted with EtOAc
  8. washthe combined organic extracts were washed successively with 1M NaOH, H2O and saturated aqueous NaCl
  9. customdried
  10. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-4061484cf68d4108bc84d27e0c9f8955
Source dataset
uspto-grants-1998_02
Patent number
US05719182

Reaction notes

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