Nitric Acid → HCID 54574717, compound
Reaction equation
[CH3:1][CH:2]([CH2:5][CH2:6][CH3:7])[CH:3]=[CH2:4].[N+:8]([O-])([OH:10])=[O:9]>>[CH3:1][C:2]([CH2:5][CH2:6][CH3:7])=[CH:3][CH2:4][N+:8]([O-:10])=[O:9]Participants
3
Conditions
- Temperature
- 65 °C
Procedure
3-Methyl-1-hexene (22.2 mL, 0.15 moles) was mixed with concentrated nitric acid (18 mL, 0.28 moles) at room temperature. With rapid stirring the solution was heated to 65° C. for 3 hours. The heat was removed and the solution stirred an additional 30 min. The organic layer was separated and washed with a saturated sodium chloride solution (3×15 mL) then dried over magnesium sulfate. Vacuum distillation (20 Torr, 28° C.) removed unreacted 3-methyl-1-hexene. A yellow oil remained. Gas chromatography and IR spectroscopy indicate both cis- and trans-3-methyl-1-nitro-2-hexene are present along with a small amount of 1-nitro-2-hexanol. These structures were confirmed by IR and GC analysis.