Sodium Iodide → 1-[2,6-bis(benzyloxy)phenyl]ethanone

HRID 1767303Notes

Reaction equation

HRID 1767303 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+].[I-].[Na+]>CC(C)=O>[CH2:12]([O:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH2:9][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:2]=2)[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 5238Sodium IodideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 696872',6'-Dihydroxyacetophenone

Product 1

HCID 8388661-[2,6-bis(benzyloxy)phenyl]ethanoneYield 91.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of (2′,6′-dihydroxy)acetophenone (25.0 g, 164 mmol), benzyl bromide (40 mL, 337 mmol), potassium carbonate (136 g, 986 mmol) and sodium iodide (2.5 g, 16 mmol) in acetone (500 mL) was stirred at reflux overnight. The mixture was concentrated under reduced pressure, and diluted with ethyl acetate (500 mL) and water (250 mL). The separated aqueous phase was extracted with ethyl acetate (200 mL×2). The combined organic phase was washed with brine (100 mL), dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was triturated with hexane, collected by filtration, washed with hexane and dried under reduced pressure to give 1-[2,6-bis(benzyloxy)phenyl]ethanone (24.9 g, yield; 46%).

Workup

  1. temperatureat reflux overnight
  2. concentrationThe mixture was concentrated under reduced pressure
  3. additiondiluted with ethyl acetate (500 mL) and water (250 mL)
  4. extractionThe separated aqueous phase was extracted with ethyl acetate (200 mL×2)
  5. washThe combined organic phase was washed with brine (100 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was triturated with hexane
  10. filtrationcollected by filtration
  11. washwashed with hexane
  12. customdried under reduced pressure

Sources & evidence

ORD record
ord-83be890f63dd4ff887bc9a6111108d24
Source dataset
uspto-grants-2007_06
Patent number
US07232909B2

Reaction notes

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