Nitric Acid → HCID 131711051, compound

HRID 1679148Notes

Reaction equation

HRID 1679148 reaction equation
[C:1]([O:4]C(=O)C)(=[O:3])[CH3:2].[N+:8]([O-:11])(O)=[O:9].[CH2:12]=[CH:13][CH:14]=[CH:15][CH2:16][CH3:17]>>[N+:8]([CH2:12][CH:13]=[CH:14][CH:15]([O:4][C:1](=[O:3])[CH3:2])[CH2:16][CH3:17])([O-:11])=[O:9]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 116021,​3-​Hexadiene

Product 1

HCID 131711051HCID 131711051, compound

Conditions

Temperature
25 °C

Procedure

To 166 ml. of acetic anhydride was added 90% nitric acid (27.7 g.) under cooling at 25° C. over a 45 minute period. After an additional 5 minutes of stirring 20 g. of 1,3-hexadiene was added dropwise at 25° C. over 1 hour. Ice cooling was employed as required. The reaction was completed by stirring the mixture for an additional hour, followed by quenching in ice and water. Extraction with methylenechloride, washing with water, drying of the organic layers over anhydrous sodium sulfate and evaporation of the solvent and excess acetic anhydride resulted in 47.0 g. of a crude reaction product. Column chromatography and careful bulb to bulb distillation (oven 120° C., 0.5 mmHg) yielded actic acid (1-nitro-2-hexen-4-yl)ester.

Workup

  1. stirringby stirring the mixture for an additional hour
  2. customby quenching in ice
  3. extractionExtraction with methylenechloride
  4. washwashing with water
  5. dry with materialdrying of the organic layers over anhydrous sodium sulfate and evaporation of the solvent and excess acetic anhydride
  6. customresulted in 47.0 g
  7. customof a crude reaction product
  8. distillationColumn chromatography and careful bulb to bulb distillation (oven 120° C., 0.5 mmHg)

Sources & evidence

ORD record
ord-58175263f2f44ad698344ee8a30f5029
Source dataset
uspto-grants-1978_03
Patent number
US04079076

Reaction notes

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