Nitric Acid → 1-Acetoxy-4-nitro-2-cycloheptene

HRID 1856499Notes

Reaction equation

HRID 1856499 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[CH2:18][CH2:17]CC=[CH:14][CH:13]=1>>[C:5]([O:4][CH:1]1[CH2:17][CH2:18][CH2:12][CH:13]([N+:8]([O-:11])=[O:9])[CH:14]=[CH:2]1)(=[O:7])[CH3:6]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 199691,3-Cycloheptadiene

Product 1

HCID 233454741-Acetoxy-4-nitro-2-cycloheptene

Conditions

Temperature
25 °C

Procedure

To 0.6 Mol of acetic anhydride were added at 25° C. 0.16 Mol 90% HNO3 over 30 minutes. The mixture was stirred for an additional 15 minutes before 0.1 Mol of 1,3-cyclo-heptadiene was added over a 45 minute period, maintaining the temperature at 25° C. The reaction mixture was stirred for an additional 45 minutes before it was poured onto ice water and extracted with methylene chloride. An oily residue (100.5% weight yield) was obtained, which was purified by column chromatography, using silica gel and benzene/ethylacetate 4:1 as eluent. The product has the appearance of a yellow oil.

Workup

  1. additionwas added over a 45 minute period
  2. additionwas poured onto ice water
  3. extractionextracted with methylene chloride
  4. customAn oily residue (100.5% weight yield)
  5. customwas obtained
  6. customwhich was purified by column chromatography

Sources & evidence

ORD record
ord-b40b04223e8c4acf90dad3afdcdb7e10
Source dataset
uspto-grants-1980_08
Patent number
US04219660

Reaction notes

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