Phenylacetone → HCID 53698084, compound

HRID 1076319Notes

Reaction equation

HRID 1076319 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)[CH:14]=[CH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(COC)OC>[C:3]1([CH:9]([CH2:13][CH:14]=[CH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10](=[O:12])[CH3:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 7678PhenylacetoneHCID 24758Sodium hydrideHCID 94242Benzene, (3-chloro-1-propenyl)-

Product 1

HCID 53698084HCID 53698084, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent3×

Procedure

Sodium hydride (10.5 g., 0.25 mole, oil dispersion) is suspended in glyme (200 ml.) and phenyl acetone (33.5 g., 0.25 mole) in glyme (25 ml.) is added dropwise with stirring. After complete addition, the mixture is heated to reflux for 0.5 hours. The mixture is cooled in a cold water bath and a solution of cinnamyl chloride (38 g., 0.25 mole) in glyme (25 ml.) is added dropwise. When addition is complete, the mixture is refluxed for 5 hours then allowed to cool. After filtration of inorganic salts and removal of solvent from the filtrate, vacuum distillation provides 44 g., b.p. 128°-134°/0.07-0.1 mm.

Workup

  1. additionAfter complete addition
  2. temperaturethe mixture is heated
  3. temperatureto reflux for 0.5 hours
  4. temperatureThe mixture is cooled in a cold water bath
  5. additionWhen addition
  6. temperaturethe mixture is refluxed for 5 hours
  7. temperatureto cool
  8. filtrationAfter filtration of inorganic salts and removal of solvent
  9. distillationfrom the filtrate, vacuum distillation
  10. customprovides 44 g

Sources & evidence

ORD record
ord-ae4a4a8514b54bfc865ac122c0bff0d8
Source dataset
uspto-grants-1976_05
Patent number
US03956374

Reaction notes

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