Reaktion #44972

Reaktionsgleichung

sodium hydride

2-(benzyloxy)ethanol

chloroacetic acid

→

[2-(benzyloxy)ethoxy]acetic acid

Ausbeute 102.4%

Lösungsmittel

—

oil

N,N-dimethylacetamide

N,N-dimethylacetamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooling
2. 2
   Temperaturthe reaction solution is cooled with ice
3. 3
   workup.STIRRINGThe mixture is then stirred at room temperature for 11 hours
4. 4
   EinengenThe reaction solution is concentrated under reduced pressure
5. 5
   workup.ADDITIONto the resulting residue is added aqueous sodium hydrogen carbonate solution
6. 6
   Waschenthe mixture is washed with diethyl ether
7. 7
   Extraktionextracted with ethyl acetate
8. 8
   WaschenThe organic layer is washed with saturated brine
9. 9
   Trocknendried over sodium sulfate
10. 10
    Sonstigeevaporated
11. 11
    Sonstigeto remove solvent under reduced pressure

Vorschrift

Sixty % sodium hydride in oil (6.80 g) is suspended in N,N-dimethylacetamide (80 ml) and a solution of 2-(benzyloxy)ethanol (12.9 g) in N,N-dimethylacetamide (50 ml) is added dropwise to the mixture over 10 minutes under ice-cooling. After stirring at room temperature for 15 minutes, the reaction solution is cooled with ice, and thereto is added chloroacetic acid (8.13 g) in small portions. The mixture is then stirred at room temperature for 11 hours. The reaction solution is concentrated under reduced pressure, and to the resulting residue is added aqueous sodium hydrogen carbonate solution and the mixture is washed with diethyl ether. The aqueous layer is acidified with conc. hydrochloric acid, and then extracted with ethyl acetate. The organic layer is washed with saturated brine, dried over sodium sulfate and evaporated to remove solvent under reduced pressure to give [2-(benzyloxy)ethoxy]acetic acid (18.24 g).

Quelle