Nitric Acid → HCID 54574717, compound

HRID 638470Notes

Reaction equation

HRID 638470 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

Reactant 2

HCID 944Nitric AcidHCID 188481-Hexene, 3-methyl-

Product 1

HCID 54574717HCID 54574717, compound

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.

Workup

  1. customThe heat was removed
  2. stirringthe solution stirred an additional 30 min
  3. customThe organic layer was separated
  4. washwashed with a saturated sodium chloride solution (3×15 mL)
  5. dry with materialthen dried over magnesium sulfate
  6. distillationVacuum distillation (20 Torr, 28° C.)
  7. customremoved unreacted 3-methyl-1-hexene

Sources & evidence

ORD record
ord-fcc005098f274feaa1364c2902050e3f
Source dataset
uspto-grants-1985_12
Patent number
US04561862

Reaction notes

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