Reacción #2383807

Ecuación de reacción

2-nitroethanol

sodium acetate

acetic anhydride

2-nitroethanol

→

2-nitroethylacetate

Disolventes

ethyl acetate

brine

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe orange reaction mixture was stirred at 0-5° C. for an additional hour
2. 2
   Temperaturathe exotherm of the reaction increased the temperature to 30° C.
3. 3
   Temperaturathe mixture was cooled with an ice bath to 20° C
4. 4
   workup.STIRRINGThe reaction was then stirred at ambient temperature under N2 overnight
5. 5
   OtroThe layers were separated
6. 6
   Extracciónthe bottom aqueous layer was extracted again with ethyl acetate (25 mL)
7. 7
   LavadoThe combined ethyl acetate layers were washed once with saturated brine (50 mL)
8. 8
   Secadodried (MgSO4)
9. 9
   Filtraciónfiltered
10. 10
    Concentraciónconcentrated

Procedimiento

A mixture of sodium acetate (6.4 g, 78 mmol) and acetic anhydride (30 mL, 330 mmol) was stirred at 0-5° C. To this slurry was added 2-nitroethanol (30 g, 280 mmol) dropwise over a period of approximately 1 hour. After the 2-nitroethanol addition, the orange reaction mixture was stirred at 0-5° C. for an additional hour and then at ambient temperature for approximately 70 min, the exotherm of the reaction increased the temperature to 30° C. and the mixture was cooled with an ice bath to 20° C. The reaction was then stirred at ambient temperature under N2 overnight. The reaction mixture was diluted with ethyl acetate (EtOAc, 40 mL) and saturated brine (80 mL). The layers were separated and the bottom aqueous layer was extracted again with ethyl acetate (25 mL). The combined ethyl acetate layers were washed once with saturated brine (50 mL), dried (MgSO4), filtered and concentrated to afford 38 g of 2-nitroethylacetate as a reddish orange oil.

Fuente