Acetophenone → N,N-diethyl-4-(1-phenylethenyl)aniline

HRID 579933Notes

Reaction equation

HRID 579933 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=O)[CH3:2].[CH2:10]([N:12]([CH2:21][CH3:22])[C:13]1[CH:18]=[CH:17][C:16]([Mg]Br)=[CH:15][CH:14]=1)[CH3:11].[Mg].BrC1C=CC(N(CC)CC)=CC=1.[Cl-].[NH4+]>O1CCCC1.C1C=CC=CC=1>[CH2:10]([N:12]([CH2:21][CH3:22])[C:13]1[CH:18]=[CH:17][C:16]([C:1]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[CH2:2])=[CH:15][CH:14]=1)[CH3:11]

Participants

8

Reactant 5

HCID 7410AcetophenoneHCID 16328Benzenamine, 4-bromo-N,N-diethyl-HCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 178463831HCID 178463831, compound

Product 1

HCID 14150475N,N-diethyl-4-(1-phenylethenyl)aniline

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

After adding dropwise 100 ml of a benzene solution containing 8 g of acetophenone to a tetrahydrofuran solution of 4-diethylaminophenylmagnesium bromide prepared from 2 g of magnesium, 16 g of 4-bromodiethylaniline, and 100 ml of tetrahydrofuran, stirring was continued under reflux for 5 hours. After cooling, 200 ml of a saturated aqueous ammonium chloride solution was added thereto. The mixture was subjected to hydrolysis, and an organic layer was separated and washed with water. After distilling off the solvent, the residue was dissolved in benzene, and the solution was stirred and refluxed with the addition of 0.1 g of p-toluenesulfonic acid for one hour. After distilling off the solvent, the residue was dissolved in benzene, and the product was separated and purified by silica gel column chromatography.

Workup

  1. temperatureunder reflux for 5 hours
  2. temperatureAfter cooling
  3. customThe mixture was subjected to hydrolysis
  4. customan organic layer was separated
  5. washwashed with water
  6. distillationAfter distilling off the solvent
  7. dissolutionthe residue was dissolved in benzene
  8. stirringthe solution was stirred
  9. temperaturerefluxed with the addition of 0.1 g of p-toluenesulfonic acid for one hour
  10. distillationAfter distilling off the solvent
  11. dissolutionthe residue was dissolved in benzene
  12. customthe product was separated
  13. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-960e4de827e14df2b3b7e25a1300cacf
Source dataset
uspto-grants-1988_06
Patent number
US04751163

Reaction notes

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