(2-Bromoethyl)cyclohexane → (2-Nitroethyl)cyclohexane

Temperature

25 °C

An oven-dried 1 liter 3-necked flask fitted with dropping funnel, thermometer and 31 g sodium nitrite. The mixture was stirred at 5° C. while 50 g 2-cyclohexylethylbromide (Aldrich) was added over 5 minutes. The cooling bath was removed and the mixture was stirred at 25° C. for 18 hours, poured into 1.5 l cold water and the mixture was repeatedly extracted (4×150 ml) with petroleum ether which was washed with water (2×10 ml) and dried over magnesium sulfate. The solvent was removed at reduced pressure using a rotary evaporator and the residue was distilled through an 8" Vigreux column giving 18.3 g (41%) of the desired product boiling at 70°-80° C. and 2 mm Hg, preceded by 8 g of lower-boiling material gave 16.4 g, 40%, bp 62°-65° C. at 0.5 mm Hg of the title product.

1. customAn oven-dried 1 liter 3-necked flask fitted
2. additionwas added over 5 minutes
3. customThe cooling bath was removed
4. additionpoured into 1.5 l cold water
5. extractionthe mixture was repeatedly extracted (4×150 ml) with petroleum ether which
6. washwas washed with water (2×10 ml)
7. dry with materialdried over magnesium sulfate
8. customThe solvent was removed at reduced pressure
9. customa rotary evaporator
10. distillationthe residue was distilled through an 8" Vigreux column

ORD record

ord-48558294ee744d3bab1134f04f5e1eb1

Source dataset

uspto-grants-1989_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04855303