Dimethylformamide → 3-(p-Diethylaminophenyl)-3-phenylacrolein

HRID 579934Notes

Reaction equation

HRID 579934 reaction equation
P(Cl)(Cl)(Cl)=O.CN(C)[CH:8]=[O:9].[CH2:11]([N:13]([CH2:28][CH3:29])[C:14]1[CH:19]=[CH:18][C:17]([C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH2:21])=[CH:16][CH:15]=1)[CH3:12].C([O-])(=O)C.[Na+]>ClCCCl.O>[CH2:28]([N:13]([CH2:11][CH3:12])[C:14]1[CH:19]=[CH:18][C:17]([C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:21][CH:8]=[O:9])=[CH:16][CH:15]=1)[CH3:29]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 517045Sodium AcetateHCID 14150475N,N-diethyl-4-(1-phenylethenyl)aniline

Product 1

HCID 542012503-(p-Diethylaminophenyl)-3-phenylacroleinYield 57%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent2×HCID 962WaterSolvent

Procedure

After adding dropwise 3.9 g of phosphorus oxychloride to a solution of 2.2 g of dimethylformamide (DMF) and 50 ml of 1,2-dichloroethane at from 0° to 5° C., the mixture was stirred at that temperature for 30 minutes. Then, a solution of 5.2 g of 1-(p-diethylaminophenyl)-1-phenylethylene in 50 ml of 1,2-dichloroethane solution was added dropwise thereto at that temperature over 30 minutes, and the mixture was reacted from 5 hours at room temperature. Hydrolysis was conducted with an addition of 100 cc of water containing 10 g of sodium acetate. After separating and water-washing an organic layer, the solvent was distilled off to obtain 4.8 g of an oily substance which was subsequently separated and purified on silica gel column chromatography to obtain 3.3 g (yield: 57% (theory)) of an oily product.

Workup

  1. waitat that temperature over 30 minutes
  2. customthe mixture was reacted from 5 hours at room temperature
  3. customHydrolysis
  4. customAfter separating
  5. washwater-washing an organic layer
  6. distillationthe solvent was distilled off
  7. customto obtain 4.8 g of an oily substance which
  8. customwas subsequently separated
  9. custompurified on silica gel column chromatography
  10. customto obtain 3.3 g (yield: 57% (theory)) of an oily product

Sources & evidence

ORD record
ord-cf1621eb27e3468a908d52bf5fbf82f6
Source dataset
uspto-grants-1988_06
Patent number
US04751163

Reaction notes

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