Nitric Acid → HCID 54238171, compound

HRID 638472Notes

Reaction equation

HRID 638472 reaction equation
[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[N+:13]([O-])([OH:15])=[O:14]>>[N+:13]([CH2:1][CH:2]=[CH:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])([O-:15])=[O:14]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 81831-Dodecene

Product 1

HCID 54238171HCID 54238171, compound

Conditions

Temperature
100 °C

Procedure

1-Dodecene (222 mL, 1.0 mole) and concentrated nitric acid (96 mL, 1.5 moles) were mixed together at room temperature. The solution was heated to 100° C. for 4 hours with rapid stirring then cooled to room temperature. The organic layer separated and washed with a saturated sodium chloride solution (3×75 mL). After drying over magnesium sulfate and filtering, the orange oil was vacuum distilled (0.5 Torr, 36° C.) which removed unreacted 1-dodecene. The remaining orange/red oil is a mixture containing 1-nitro-2-dodecene and 1-nitro-2-dodecanol. This oil was further reacted with methanesulfonyl chloride and triethylamine to dehydrate the alcohol and produce more 1-nitro-2-dodecene. After this dehydration step, the structure of 1-nitro-2-dodecene was confirmed by IR and GC analysis.

Workup

  1. temperaturethen cooled to room temperature
  2. customThe organic layer separated
  3. washwashed with a saturated sodium chloride solution (3×75 mL)
  4. dry with materialAfter drying over magnesium sulfate
  5. filtrationfiltering
  6. distillationdistilled (0.5 Torr, 36° C.) which
  7. customremoved unreacted 1-dodecene
  8. additioncontaining 1-nitro-2-dodecene and 1-nitro-2-dodecanol
  9. customThis oil was further reacted with methanesulfonyl chloride and triethylamine

Sources & evidence

ORD record
ord-104cf1dd1c7049108a3563153a7a8e8e
Source dataset
uspto-grants-1985_12
Patent number
US04561862

Reaction notes

Loading…