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

HRID 1934296Notes

Reaction equation

HRID 1934296 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

After adding 55.8 g of ice-cooled phosphoryl chloride to 26.6 g of dimethylformamide, a solution of 63.0 g of the 2-(N-ethylanilino)ethyl acetate in 40 ml of dimethylformamide was slowly added at room temperature, this was caused to react for 6 hours at room temperature while stirring, and then poured into an aqueous solution of 150 g of sodium acetate under ice cooling. An organic layer was extracted with ethyl acetate and the solvent was boiled off under reduced pressure. This was refined by silica gel column chromatography to yield 60.2 g of 2-(ethyl(4-formylphenyl)amino)ethyl acetate.

Workup

  1. customto react for 6 hours at room temperature
  2. extractionAn organic layer was extracted with ethyl acetate

Sources & evidence

ORD record
ord-cd1897f09e154f11a129d2603cfaff4e
Source dataset
uspto-grants-2002_05
Patent number
US06383714B1

Reaction notes

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