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

HRID 2086531Notes

Reaction equation

HRID 2086531 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]-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To 16.1 g of dimethylformamide was dropwise added 33.7 g of phosphoryl chloride while stirring under ice cooling. Further, 30 ml of a solution of 41.5 g of 2-(ethylphenylamino)ethyl acetate in dimethylformamide was added dropwise, and this mixture was stirred for 5 hours at 40° C. This reaction solution was poured into 1,000 ml of sodium acetate aqueous solution. An organic layer was extracted with ethyl acetate, washed with water, and then dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting coarse product was purified by silica gel column chromatography to obtain 35.3 g of 2-(ethyl(4-formylphenyl)amino)ethyl acetate.

Workup

  1. stirringthis mixture was stirred for 5 hours at 40° C
  2. extractionAn organic layer was extracted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe resulting coarse product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7d8a47a366904d2183c1788375cbd120
Source dataset
uspto-grants-2004_04
Patent number
US06727037B2

Reaction notes

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