Nitromethane → 1-(Nitromethyl)cyclobutanol

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.

1. customSome of the ethanol was removed under reduced pressure, and water (100 mL)
2. additionwas added
3. extractionThe resulting mixture was extracted with ethyl acetate (3×150 mL)
4. washThe combined extracts were washed sequentially with water (2×80 mL) and brine (40 mL)
5. dry with materialdried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. distillationThe residue was purified by vacuum distillation under high vacuum at 70° C.

ORD record

ord-e7d9c8171a6047729b4865442ad3e73b

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08541438B2