Potassium Cyanide → 3-Cyano-3-phenylpropanoic acid

HRID 845766Notes

Reaction equation

HRID 845766 reaction equation
[CH:1](=[C:8]([C:12]([O-:14])=[O:13])C([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-:15]#[N:16].[K+]>C(O)C.O>[C:15]([CH:1]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:8][C:12]([OH:14])=[O:13])#[N:16]

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 21863568Benzalmalonate

Product 1

HCID 111946253-Cyano-3-phenylpropanoic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of benzalmalonate (124 g., 0.5 mole) in ethanol (560 ml.) and water (240 ml.) was heated at reflux for 60 hours with potassium cyanide (45 g., 0.7 mole). The solution was cooled, concentrated to remove ethanol, and then acidified with concentrated hydrochloric acid. The product was extracted with dichloromethane, and the extracts were washed with brine, dried over anhydrous sodium sulfate, and concentrated. The residue was dissolved in ethyl acetate (500 ml.) and treated with dicyclohexylamine (82 ml.) to yield 118 g. (67%) of white crystals which were collected by filtration and washed sequentially with ethyl acetate and ether and dried. A suitable cation-exchange resin in the acid form, such as Dowex® 50x8-100 ion-exchange resin, (20 g.) was washed with acetone and suspended in methanol (130 ml.) with dicyclohexylammonium salt (15 g.). After stirring at ambient temperature for 1 hour, the cation exchange resin was removed by filtration and the filtrate was concentrated to yield 3-cyano-3-phenylpropionic acid as an oil.

Workup

  1. temperatureThe solution was cooled
  2. concentrationconcentrated
  3. customto remove ethanol
  4. extractionThe product was extracted with dichloromethane
  5. washthe extracts were washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. dissolutionThe residue was dissolved in ethyl acetate (500 ml.)
  9. additiontreated with dicyclohexylamine (82 ml.)
  10. customto yield 118 g
  11. filtration(67%) of white crystals which were collected by filtration
  12. washwashed sequentially with ethyl acetate and ether
  13. customdried
  14. washA suitable cation-exchange resin in the acid form, such as Dowex® 50x8-100 ion-exchange resin, (20 g.) was washed with acetone
  15. customthe cation exchange resin was removed by filtration
  16. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-a96b828d881f49bea515f486b1831ac9
Source dataset
uspto-grants-1988_07
Patent number
US04760089

Reaction notes

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