Cyclohexene → HCID 19751984, compound

HRID 483296Notes

Reaction equation

HRID 483296 reaction equation
[N+:1]([C:4]1[C:5]([O:16][CH3:17])=[C:6]([Cl:15])[CH:7]=[C:8]([N+:12]([O-])=O)[C:9]=1[O:10][CH3:11])([O-:3])=[O:2].C1CCCCC=1>[Pd].C(O)C>[NH2:12][C:8]1[C:9]([O:10][CH3:11])=[C:4]([N+:1]([O-:3])=[O:2])[C:5]([O:16][CH3:17])=[C:6]([Cl:15])[CH:7]=1

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 2849581-chloro-2,4-dimethoxy-3,5-dinitrobenzene

Product 1

HCID 19751984HCID 19751984, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The mixture consisting of 0.2 mole (52.5 g) of 3,5-dinitro-2,4-dimethoxychlorobenzene, 15.9 g of palladium on charcoal (10%) in 260 ml of absolute ethanol containing 110 ml of cyclohexene was heated to reflux for 1 hour. The catalyst was removed by filtration. After evaporation to dryness under vacuum, an oil was obtained which crystallized after an addition of iced water. After thorough draining and drying, the product obtained was recrystallized from a benzene and cyclohexane mixture. It melted at 68° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1 hour
  3. customThe catalyst was removed by filtration
  4. customAfter evaporation to dryness under vacuum
  5. customan oil was obtained which
  6. customcrystallized
  7. additionafter an addition of iced water
  8. customAfter thorough draining and drying
  9. customthe product obtained
  10. customwas recrystallized from a benzene and cyclohexane mixture

Sources & evidence

ORD record
ord-c2add4bde2684875b01d4c062c4e85f8
Source dataset
uspto-grants-1993_07
Patent number
USRE034300

Reaction notes

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