Reaktion #73073

Reaktionsgleichung

nitromethane

sodium ethoxide

cyclobutanone

→

1-(nitromethyl)cyclobutanol

Ausbeute 49.3%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeSome of the ethanol was removed under reduced pressure, and water (100 mL)
2. 2
   workup.ADDITIONwas added
3. 3
   ExtraktionThe resulting mixture was extracted with ethyl acetate (3×150 mL)
4. 4
   WaschenThe combined extracts were washed sequentially with water (2×80 mL) and brine (40 mL)
5. 5
   Trocknendried over sodium sulfate
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated under reduced pressure
8. 8
   workup.DISTILLATIONThe residue was purified by vacuum distillation under high vacuum at 70° C.

Vorschrift

Under a nitrogen atmosphere, nitromethane (116 mL, 2.14 mol) and sodium ethoxide (2.6 g of 96% pure material, 36 mmol) were sequentially added to a solution of cyclobutanone (50.0 g, 713 mmol) in ethanol (71 mL), and the resulting solution was stirred at room temperature for 4 days. Some of the ethanol was removed under reduced pressure, and water (100 mL) was added. The resulting mixture was extracted with ethyl acetate (3×150 mL). The combined extracts were washed sequentially with water (2×80 mL) and brine (40 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by vacuum distillation under high vacuum at 70° C. to provide 46.1 g of 1-(nitromethyl)cyclobutanol as an orange liquid.

Quelle