Phenylacetone → 3-Phenyl-6-(m-chlorophenyl)-5-hexen-2-one

HRID 1076313Notes

Reaction equation

HRID 1076313 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:15]=[C:16]([CH:21]=[CH:22][CH:23]=1)[CH:17]=[CH:18][CH2:19]Br>C(COC)OC>[Cl:13][C:14]1[CH:15]=[C:16]([CH:17]=[CH:18][CH2:19][CH:9]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[C:10](=[O:12])[CH3:11])[CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 7678PhenylacetoneHCID 24758Sodium hydrideHCID 54032824m-Chlorocinnamyl bromide

Product 1

HCID 537053773-Phenyl-6-(m-chlorophenyl)-5-hexen-2-one

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent3×

Procedure

Sodium hydride (25.20 g., 0.60 mole, oil dispersion) is suspended in glyme (800 ml.) and phenyl acetone (80.50 g., 0.60 mole) in glyme (100 ml.) 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 m-chlorocinnamyl bromide (139 g., 0.6 mole) in glyme (100 ml.) is added dropwise. When addition is complete the mixture is refluxed for 24 hours then allowed to cool. After filtration of inorganic salts and removal of solvent from the filtrate, vacuum distillation provides 36.11 g., b.p. 158.5°-163°/0.1 mm.

Workup

  1. additionAfter complete addition the mixture
  2. temperatureis heated
  3. temperatureto reflux for one hour
  4. additionWhen addition
  5. temperatureis refluxed for 24 hours
  6. temperatureto cool
  7. filtrationAfter filtration of inorganic salts and removal of solvent
  8. distillationfrom the filtrate, vacuum distillation
  9. customprovides 36.11 g

Sources & evidence

ORD record
ord-84d02f43db0a4194a5d81565a0c94a27
Source dataset
uspto-grants-1976_05
Patent number
US03956374

Reaction notes

Loading…