Nitric Acid → HCID 13444163, compound

HRID 1856500Notes

Reaction equation

HRID 1856500 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].[N+:8]([O-:11])(O)=[O:9].[CH:12]1[CH2:16]C=C[CH:13]=1>>[C:5]([O:4][CH:1]1[CH2:16][CH:12]([N+:8]([O-:11])=[O:9])[CH:13]=[CH:2]1)(=[O:7])[CH3:6]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 7612CyclopentadieneHCID 7918Acetic Anhydride

Product 1

HCID 13444163HCID 13444163, compound

Conditions

Temperature
25 °C

Procedure

To 0.6 Mol of acetic anhydride were added at 25° C. 0.163 Mol 90% HNO3 over 45 minutes. The mixture was stirred for an additional 20 minutes before 0.1 Mol cyclopentadiene was added over a 1 hour period, maintaining the temperature at 25° C. The reaction mixture was stirred for an additional hour before it was poured onto ice water and extracted with methylene chloride. An oily residue (120% weight yield) was obtained. An aliquot was purified via Kugelrohr distillation removing first acetic acid/acetic anhydride followed by the product.

Workup

  1. additionwas added over a 1 hour period
  2. additionwas poured onto ice water
  3. extractionextracted with methylene chloride
  4. customAn oily residue (120% weight yield)
  5. customwas obtained
  6. distillationAn aliquot was purified via Kugelrohr distillation
  7. customremoving first acetic acid/acetic anhydride

Sources & evidence

ORD record
ord-f82794b4bf8e4110b2fe8f3c5461b7e0
Source dataset
uspto-grants-1980_08
Patent number
US04219660

Reaction notes

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