Acetone → 1-Methoxy-3-phenylpropan-2-one

HRID 1359416Notes

Reaction equation

HRID 1359416 reaction equation
CC(C)=O.[CH3:5][O:6][CH2:7][CH:8]([OH:16])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CC(O)C>[CH3:5][O:6][CH2:7][C:8]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:16]

Participants

4

Reactant 2

HCID 180AcetoneHCID 135125601-Methoxy-3-phenyl-2-propanol

Product 1

HCID 117449711-Methoxy-3-phenylpropan-2-oneYield 73.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

20.4 ml of a Jone's reagent was slowly added dropwise into 200 ml of an acetone solution containing 5.1 g of 1-methoxy-3-phenyl-2-propanol. After stirring for 30 minutes at room temperature, 30 ml of 2-propanol was slowly added to the reaction solution. After removing the solvent, water was added thereto and the mixture was extracted with ethyl acetate. The organic phase was washed with brine and the solvent was removed. The residue was subjected to silica gel column chromatography and elute with hexane/ethyl acetate (6:1), to give 3.7 g of the target compound.

Workup

  1. customAfter removing the solvent, water
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic phase was washed with brine
  5. customthe solvent was removed
  6. washelute with hexane/ethyl acetate (6:1)

Sources & evidence

ORD record
ord-476b05a3d40b4c35bc563713a6029d38
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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