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

HRID 1076325Notes

Reaction equation

HRID 1076325 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.[CH3:13][C:14]1[CH:15]=[C:16]([CH:21]=[CH:22][CH:23]=1)[CH:17]=[CH:18][CH2:19]Br>C(COC)OC>[C:3]1([CH:9]([CH2:19][CH:18]=[CH:17][C:16]2[CH:21]=[CH:22][CH:23]=[C:14]([CH3:13])[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 7678PhenylacetoneHCID 24758Sodium hydrideHCID 53894373m-Methylcinnamyl bromide

Product 1

HCID 537406993-Phenyl-6-(m-methylphenyl)-5-hexen-2-one

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent3×

Procedure

Sodium hydride (6 g., 0.14 mole, oil dispersion) is suspended in glyme (250 ml.) and phenyl acetone (18.6 g., 0.14 mole) in glyme (50 ml.) is added dropwise with stirring. After complete addition the mixture is heated to reflux for one hour. The mixture is cooled in a cold water bath and a solution of m-methylcinnamyl bromide (29.16 g., 0.14 mole) in glyme (50 ml.) is added dropwise. When addition is complete the mixture is refluxed for 20 hours. The cooled mixture is filtered and the filtrate is evaporated under reduced pressure. The residue is dissolved in ether and washed with dilute hydrochloric acid, water and saturated brine. After drying (MgSO4) and evaporation of ether the residue is vacuum distilled and the product is collected at 161°-164°/0.4 mm; 25.24 g.

Workup

  1. additionAfter complete addition the mixture
  2. temperatureis heated
  3. temperatureto reflux for one hour
  4. temperatureThe mixture is cooled in a cold water bath
  5. additionWhen addition
  6. temperatureis refluxed for 20 hours
  7. filtrationThe cooled mixture is filtered
  8. customthe filtrate is evaporated under reduced pressure
  9. dissolutionThe residue is dissolved in ether
  10. washwashed with dilute hydrochloric acid, water and saturated brine
  11. customAfter drying
  12. custom(MgSO4) and evaporation of ether the residue
  13. distillationdistilled
  14. customthe product is collected at 161°-164°/0.4 mm

Sources & evidence

ORD record
ord-cea62ba1406e4bc582d02f2529c49d8d
Source dataset
uspto-grants-1976_05
Patent number
US03956374

Reaction notes

Loading…