Sodium Iodide → 1-[2-(Benzyloxy)phenyl]propan-1-one

HRID 2290731Notes

Reaction equation

HRID 2290731 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:11])[CH2:9][CH3:10].[CH2:12](Cl)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:12]([O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:11])[CH2:9][CH3:10])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 691332'-Hydroxypropiophenone

Product 1

HCID 123763651-[2-(Benzyloxy)phenyl]propan-1-oneYield 91.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2'-hydroxypropiophenone (25.8 g), benzyl chloride (21.8 g), sodium iodide (2.6 g), potassium carbonate (23.8 g) and dry dimethylformamide (260 ml) was heated with stirring at 80° C. for 23 hours. The mixture was cooled and filtered and the filtrate was concentrated under reduced pressure. The residue was extracted with ether and the extract was washed with water, 1N aqueous sodium hydroxide, water, 10% hydrochloric acid, aqueous sodium hydrogen carbonate and aqueous sodium chloride in that order, dried, and concentrated to dryness to give 2'-benzyloxypropiophenone (37.9 g) as an oil.

Workup

  1. temperaturewas heated
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. extractionThe residue was extracted with ether
  6. washthe extract was washed with water, 1N aqueous sodium hydroxide, water, 10% hydrochloric acid, aqueous sodium hydrogen carbonate and aqueous sodium chloride in that order
  7. customdried
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-bf9f7e3f68324dec8824cc4f31291b7d
Source dataset
uspto-grants-1986_10
Patent number
US04618610

Reaction notes

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