Benzyl Chloride → 3,4-diphenylbutan-2-one

HRID 1076328Notes

Reaction equation

HRID 1076328 reaction equation
[H-].[Na+].[C:3]1([CH2:9][C:10](=[O:12])[CH3:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:13](Cl)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(COC)OC>[C:3]1([CH:9]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:10](=[O:12])[CH3:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 7678PhenylacetoneHCID 24758Sodium hydride

Product 1

HCID 2488503,4-diphenylbutan-2-one

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent3×

Procedure

Sodium hydride (8.4 g., 0.2 mole, oil dispersion) is suspended in glyme (400 ml.) and phenyl acetone (26.8 g., 0.2 mole) in glyme (50 ml.) is added dropwise with stirring. After complete addition the mixture is heated to reflux for one hour then cooled in a cold water bath. A solution of benzyl chloride (25.3 g., 0.2 mole) in glyme (50 ml.) is added then the mixture is refluxed for 12 hours. Removal of the inorganic salts by filtration followed by vacuum distillation of the residue gives 31.06 g., b.p 104°-107°/0.1 mm

Workup

  1. additionAfter complete addition the mixture
  2. temperatureis heated
  3. temperatureto reflux for one hour
  4. temperaturethen cooled in a cold water bath
  5. temperaturethe mixture is refluxed for 12 hours
  6. customRemoval of the inorganic salts
  7. filtrationby filtration
  8. distillationfollowed by vacuum distillation of the residue
  9. customgives 31.06 g
  10. customb.p 104°-107°/0.1 mm

Sources & evidence

ORD record
ord-32565c39c3654156ad749da8d6274fb3
Source dataset
uspto-grants-1976_05
Patent number
US03956374

Reaction notes

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