Phenylacetone → HCID 54240293, compound

HRID 1076309Notes

Reaction equation

HRID 1076309 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.[Cl:13][C:14]1[CH:23]=[CH:22][CH:21]=[CH:20][C:15]=1[CH:16]=[CH:17][CH2:18]Br>C(COC)OC.CCOCC>[Cl:13][C:14]1[CH:23]=[CH:22][CH:21]=[CH:20][C:15]=1[CH:16]=[CH:17][CH2:18][CH:9]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[C:10](=[O:12])[CH3:11]

Participants

6

Reactant 3

HCID 7678PhenylacetoneHCID 24758Sodium hydrideHCID 53423560HCID 53423560, compound

Product 1

HCID 54240293HCID 54240293, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 80711,2-DimethoxyethaneSolvent2×

Procedure

Sodium hydride (6.30 g., 0.15 mole, oil dispersion) is suspended in glyme (200 ml.) and phenyl acetone (20.13 g., 0.15 mole) is added dropwise with stirring. After complete addition, the mixture is heated to reflux for one hour. The mixture is cooled to room temperature, and a solution of crude o-chlorocinnamyl bromide (39.05 g., 0.17 mole) in glyme (100 ml.) is added dropwise with stirring. When addition is complete, the mixture is heated on a steam bath for 24 hours then allowed to cool. Filtration and removal of solvent in vacuo produces a yellow oil. This oil is taken up in ether (400 ml.), washed with a very dilute hydrochloric acid solution, followed by a washing with brine, and is finally dried over Na2SO4. Filtration and removal of solvent in vacuo yields the crude product as a dark oil. Vacuum distillation provides 24.9 g., b.p. 153°-155°/0.1 mm.

Workup

  1. additionAfter complete addition
  2. temperaturethe mixture is heated
  3. temperatureto reflux for one hour
  4. stirringwith stirring
  5. additionWhen addition
  6. temperaturethe mixture is heated on a steam bath for 24 hours
  7. temperatureto cool
  8. filtrationFiltration and removal of solvent in vacuo
  9. customproduces a yellow oil
  10. washwashed with a very dilute hydrochloric acid solution
  11. dry with materialis finally dried over Na2SO4
  12. filtrationFiltration and removal of solvent in vacuo

Sources & evidence

ORD record
ord-108000df8c1b46fe976d36512910c7fd
Source dataset
uspto-grants-1976_05
Patent number
US03956374

Reaction notes

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