Ethanol → 1287-16-7

HRID 343764Notes

Reaction equation

HRID 343764 reaction equation
[C-:1]1(CC#N)[CH:5]=[CH:4][CH:3]=[CH:2]1.[CH-:9]1[CH:13]=[CH:12][CH:11]=[CH:10]1.[Fe+2:14].[OH-:15].[K+].[CH2:17]([OH:19])[CH3:18]>O>[C-:9]1([CH2:18][C:17]([OH:15])=[O:19])[CH:13]=[CH:12][CH:11]=[CH:10]1.[CH-:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[Fe+2:14]

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium Hydroxide2×HCID 129667418HCID 129667418, compound

Product 1

HCID 157685011287-16-7

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4.10 g (18.2 mmol) of ferrocenylacetonitrile are dissolved in 80 ml of ethanol. 10.08 g of KOH (180 mmol) are dissolved in 80 ml of water. The potassium hydroxide solution is poured into the first solution and the mixture is brought to reflux for 4 hours. The reaction mixture is concentrated in order to remove most of the ethanol. The product is extracted with 3 times 30 ml of ether. The aqueous phase is acidified with hydrochloric acid to a pH of 1 and is again extracted with 4 times 50 ml of ethyl ether. The organic phases are combined, dried over magnesium sulfate, filtered and then evaporated. 4.20 g of ferrocenylacetic acid are obtained in the form of a yellow solid.

Workup

  1. temperatureto reflux for 4 hours
  2. concentrationThe reaction mixture is concentrated in order
  3. customto remove most of the ethanol
  4. extractionThe product is extracted with 3 times 30 ml of ether
  5. extractionis again extracted with 4 times 50 ml of ethyl ether
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-a49d4463d9224335be0966261427e6b9
Source dataset
uspto-grants-1999_01
Patent number
US05863911

Reaction notes

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