Nitric Acid → HCID 54221367, compound

HRID 1679149Notes

Reaction equation

HRID 1679149 reaction equation
[C:1]([O:4][C:5](=O)[CH3:6])(=[O:3])[CH3:2].[N+:8]([O-:11])(O)=[O:9].[CH:12]1[CH2:17]CC=[CH:14][CH:13]=1>>[N+:8]([CH:13]1[CH2:14][CH2:6][CH:5]([O:4][C:1](=[O:3])[CH3:2])[CH:17]=[CH:12]1)([O-:11])=[O:9]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 116051,3-Cyclohexadiene

Product 1

HCID 54221367HCID 54221367, compound

Procedure

To 166 ml. of acetic anhydride were dropped 27.7 g. 20% nitric acid at 25° C. under ice cooling over a 45 minute period. This was followed by the hour long addition of 19.5 g. of 1,3-cyclo hexadiene at 25° C. (ice cooling from time to time). After an additional hour stirring the reaction was poured onto ice and worked up as above. Purification over silicagel yielded acetic acid (4-nitro-cyclohex-2-en-1-yl)ester as a cis/trans mixture.

Workup

  1. additionThis was followed by the hour long addition of 19.5 g
  2. customat 25° C.
  3. additionwas poured onto ice
  4. customPurification

Sources & evidence

ORD record
ord-0a10ff2e43f04db9a10e5e1714727152
Source dataset
uspto-grants-1978_03
Patent number
US04079076

Reaction notes

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