Hydrochloric Acid → Ethyl (1-nitro-cyclohexylmethoxy)-acetate

Under the nitrogen gas atmosphere, NaH (2.32 g, 58 mmol) was added in the DMF (70 mL) solution of (1-nitro-cyclohexyl)-methanol (6.96 g, 35 mmol) which had been obtained in 1) while cooling the solution with ice, and the mixture was stirred for 20 minutes while making the temperature rise naturally. Bromoethyl acetate (9.96 g, 58.0 mmol) was dropped, and the mixture was stirred at room temperature over-night. The reaction mixture was diluted with water (200 mL), 2M hydrochloric acid (20 mL, 40 mmol) was added, and the mixture was extracted with ethyl acetate (50 mL) two times. The organic layer was washed with 5% sodium bicarbonate aqueous solution (20 mL) and water (50 mL), and then dried with anhydrous sodium sulfate. The solvents were removed by distillation under reduced pressure, the residue was refined with silica gel column chromatography (Highflash 4L, manufactured by Yamazen Corporation, the mixture of hexane and ethyl acetate of 5:1 in mixing ratio), and pale yellow oily ethyl (1-nitro-cyclohexylmethoxy)-acetate (5.47 g, 57%) was obtained.

1. customhad been obtained in 1)
2. temperaturewhile cooling the solution with ice
3. stirringthe mixture was stirred at room temperature over-night
4. additionwas added
5. extractionthe mixture was extracted with ethyl acetate (50 mL) two times
6. washThe organic layer was washed with 5% sodium bicarbonate aqueous solution (20 mL) and water (50 mL)
7. dry with materialdried with anhydrous sodium sulfate
8. customThe solvents were removed by distillation under reduced pressure
9. additionthe mixture of hexane and ethyl acetate of 5:1
10. additionin mixing ratio), and pale yellow oily ethyl (1-nitro-cyclohexylmethoxy)-acetate (5.47 g, 57%)
11. customwas obtained

ORD record

ord-abafcb7552f1492e89637c535bcc2ff7

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08178681B2