Water → 1-[2-(Benzyloxy)-6-hydroxyphenyl]ethan-1-one

HRID 660614Notes

Reaction equation

HRID 660614 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[C:3]=1[C:9](=[O:11])[CH3:10].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH2:12]([O:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[C:3]=1[C:9](=[O:11])[CH3:10])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 696872',6'-Dihydroxyacetophenone

Product 1

HCID 27751871-[2-(Benzyloxy)-6-hydroxyphenyl]ethan-1-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(2,6-dihydroxyphenyl)-ethanone (304 mg, 2 mmol) and benzyl bromide (0.255 mL, 2.1 mmol) in DMF (10 mL) is added K2CO3 (552 mg; 4 mmol) and the mixture is stirred at RT for 18 h. Water is added and the mixture is extracted with EtOAc. The organic phase is washed with water and brine then is dried over sodium sulfate. The solvent is removed under reduced pressure and the residue is purified by flash chromatography using hexane/EtOAc (10:1) as eluent to give the title compound.

Workup

  1. extractionthe mixture is extracted with EtOAc
  2. washThe organic phase is washed with water and brine
  3. dry with materialthen is dried over sodium sulfate
  4. customThe solvent is removed under reduced pressure
  5. customthe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-6934f9b747f54b6fa8d6cf9c529abafd
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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