Cyclohexene → HCID 19751984, compound

HRID 1607478Notes

Reaction equation

HRID 1607478 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-f50ef332ba794454959c186a40bd9c19
Source dataset
uspto-grants-1989_09
Patent number
US04865618

Reaction notes

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