Phosphorus oxychloride → Benzaldehyde, 4-[[2-(acetyloxy)ethyl]ethylamino]-

HRID 276744Notes

Reaction equation

HRID 276744 reaction equation
P(Cl)(Cl)(Cl)=O.[C:6]([O:9][CH2:10][CH2:11][N:12]([CH2:19][CH3:20])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:8])[CH3:7].[C:21]([O-])(=[O:23])C.[Na+]>CN(C)C=O>[C:6]([O:9][CH2:10][CH2:11][N:12]([CH2:19][CH3:20])[C:13]1[CH:18]=[CH:17][C:16]([CH:21]=[O:23])=[CH:15][CH:14]=1)(=[O:8])[CH3:7]

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 113382Ethanol, 2-(ethylphenylamino)-, 1-acetateHCID 517045Sodium Acetate

Product 1

HCID 11458991Benzaldehyde, 4-[[2-(acetyloxy)ethyl]ethylamino]-Yield 84.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

55.8 g of phosphoryl chloride cooled with ice was added to 26.6 g of N,N-dimethyl formamide. To this, a solution of 63.0 g of the 2-(N-ethylanilino)ethyl acetate and 40 ml of N,N-dimethyl formamide was added slowly at room temperature. The resulting solution was stirred for 6 hours at room temperature for reaction, and then was poured in an aqueous solution of 150 g of sodium acetate that was being cooled with ice water. The organic layer was extracted with ethyl acetate. The solvent was then distilled off under reduced pressure and purified by chromatography on silica, to obtain 60.2 g of 2-(ethyl(4-formylphenyl)amino)ethyl acetate.

Workup

  1. extractionThe organic layer was extracted with ethyl acetate
  2. distillationThe solvent was then distilled off under reduced pressure
  3. custompurified by chromatography on silica

Sources & evidence

ORD record
ord-28c3ba2832d7496783de23f90c23950f
Source dataset
uspto-grants-2002_03
Patent number
US06355396B1

Reaction notes

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