Nitroethane → HCID 131717659, compound

HRID 1681006Notes

Reaction equation

HRID 1681006 reaction equation
[C-:1]1([CH:6]=O)[CH:5]=[CH:4][CH:3]=[CH:2]1.[CH-:8]1[CH:12]=[CH:11][CH:10]=[CH:9]1.[Fe+2:13].[N+:14](CC)([O-:16])=[O:15]>C(O)(=O)C>[C-:1]1([C:6]([N+:14]([O-:16])=[O:15])=[CH:12][CH3:8])[CH:5]=[CH:4][CH:3]=[CH:2]1.[CH-:8]1[CH:12]=[CH:11][CH:10]=[CH:9]1.[Fe+2:13]

Participants

4

Reactant 2

HCID 6587NitroethaneHCID 15184314Ferrocenecarboxyaldehyde

Product 1

HCID 131717659HCID 131717659, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

Ferrocenyl-nitropropene is prepared by reacting 2.14 g ferrocenecarboxaldehyde with 2.25 g nitroethane 1.40 g ammoniumacetate and 10 ml of glacial acetic acid during 24 hours at room temperature in the dark. After heating the reaction mixture 2 hours at 100° C. and dilution with 100 ml of ice-water the formed ferrocenyl-nitropropene is extracted with diethylether. The organic solution is washed successively with Na2S2O4 -containing water, with diluted ammonia and finally with water until neutral. After drying and evaporating the diethylether, the residue obtained is recrystalized from methanol. The desired ferrocenyl-nitropropene is obtained in a yield of 80%; m.p. 48° C.; TLC: Rf (diethylamine/diethylether 5/95) 0.86.

Workup

  1. customFerrocenyl-nitropropene is prepared
  2. customduring 24 hours
  3. customat room temperature
  4. extractiondilution with 100 ml of ice-water the formed ferrocenyl-nitropropene is extracted with diethylether
  5. washThe organic solution is washed successively with Na2S2O4 -containing water, with diluted ammonia and finally with water until neutral
  6. customAfter drying
  7. customevaporating the diethylether
  8. customthe residue obtained
  9. customis recrystalized from methanol

Sources & evidence

ORD record
ord-0f6e54c83f8c4af897a220dcc0c7f7a2
Source dataset
uspto-grants-1992_12
Patent number
US05167948

Reaction notes

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