Phenylacetone → HCID 53985002, compound

HRID 1076316Notes

Reaction equation

HRID 1076316 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][CH:21]=[CH:20][C:15]=1[CH:16]=[CH:17][CH2:18]Br>C(COC)OC>[C:3]1([CH:9]([CH2:18][CH:17]=[CH:16][C:15]2[CH:20]=[CH:21][CH:22]=[CH:23][C:14]=2[CH3:13])[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 54297698HCID 54297698, compound

Product 1

HCID 53985002HCID 53985002, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent3×

Procedure

Sodium hydride (11.76 g., 0.28 mole, oil dispersion) is suspended in glyme (400 ml.) and phenyl acetone (37.57 g., 0.28 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 to room temperature and a solution of crude o-methylcinnamyl bromide (59.10 g., 0.28 mole) in glyme (50 ml.) is added dropwise. When addition is complete, the mixture is heated on a steam bath for 24 hours then allowed to cool. After filtration of inorganic salts and removal of solvent from filtrate, a dark viscous residue is obtained. Trituration of this residue with petroleum ether (30°-60°C., 100ml.) produces tan solid, yield 26.5 g., m.p. 72°-75°C.

Workup

  1. additionAfter complete addition
  2. temperaturethe mixture is heated
  3. temperatureto reflux for one hour
  4. additionWhen addition
  5. temperaturethe mixture is heated on a steam bath for 24 hours
  6. temperatureto cool
  7. filtrationAfter filtration of inorganic salts and removal of solvent from filtrate
  8. customa dark viscous residue is obtained

Sources & evidence

ORD record
ord-532d0bd5ebc34526a47dff9710093fd4
Source dataset
uspto-grants-1976_05
Patent number
US03956374

Reaction notes

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