Acetic Anhydride → 2-nitroethyl Acetate

Temperatur

2.5 °C

Ex-2a) 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.

1. stirringthe orange reaction mixture was stirred at 0-5° C. for an additional hour
2. temperaturethe exotherm of the reaction increased the temperature to 30° C.
3. temperaturethe mixture was cooled with an ice bath to 20° C
4. stirringThe reaction was then stirred at ambient temperature under N2 overnight
5. customThe layers were separated
6. extractionthe bottom aqueous layer was extracted again with ethyl acetate (25 mL)
7. washThe combined ethyl acetate layers were washed once with saturated brine (50 mL)
8. dry with materialdried (MgSO4)
9. filtrationfiltered
10. concentrationconcentrated

ORD-Eintrag

ord-ae428b2a431d43a2869f78dbfd09cb7e

Quelldatensatz

uspto-grants-2003_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06552052B2