Hydrochloric Acid → HCID 54396324, compound

HRID 1076322Notes

Reaction equation

HRID 1076322 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:23]=[CH:22][C:17]([CH:18]=[CH:19][CH2:20]Br)=[CH:16][CH:15]=1.Cl.S([O-])([O-])(=O)=O.[NH4+].[NH4+]>C(COC)OC.O>[C:3]1([CH:9]([CH2:20][CH:19]=[CH:18][C:17]2[CH:22]=[CH:23][C:14]([CH3:13])=[CH:15][CH:16]=2)[C:10](=[O:12])[CH3:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7678PhenylacetoneHCID 24758Sodium hydrideHCID 6097028Ammonium SulfateHCID 545379811-(3-Bromoprop-1-en-1-yl)-4-methylbenzene

Product 1

HCID 54396324HCID 54396324, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent3×

Procedure

Sodium hydride (6 g., 0.14 mole, oil dispersion) is suspended in glyme (200 ml.) and phenyl acetone (19.2 g., 0.14 mole) in glyme (50 ml.) is added dropwise with stirring. After complete addition the mixture is heated to reflux for 0.5 hour. The mixture is cooled in a cold water bath and a solution of p-methylcinnamyl bromide (32.2 g., 0.14 mole) in glyme (50 ml.) is added dropwise. When addition is complete, the mixture is refluxed for 18 hours then allowed to cool. Cold water (1000 ml.) is added and the mixture acidified with dilute hydrochloric acid. The mixture is saturated with ammonium sulfate and the organic material is extracted into ether. The extracts are washed with water, saturated brine, and dried (MgSO4). Filtration and removal of solvent in vacuo produces the crude product as a dark oil.

Workup

  1. additionAfter complete addition the mixture
  2. temperatureis heated
  3. temperatureto reflux for 0.5 hour
  4. temperatureThe mixture is cooled in a cold water bath
  5. additionWhen addition
  6. temperaturethe mixture is refluxed for 18 hours
  7. temperatureto cool
  8. extractionthe organic material is extracted into ether
  9. washThe extracts are washed with water, saturated brine
  10. dry with materialdried (MgSO4)
  11. filtrationFiltration and removal of solvent in vacuo

Sources & evidence

ORD record
ord-0e21ba2fcbfe4a5f92046419282f017f
Source dataset
uspto-grants-1976_05
Patent number
US03956374

Reaction notes

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