Potassium Carbonate → 3-Cyanobenzenepropanoic acid

HRID 1030952Notes

Reaction equation

HRID 1030952 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]([C:9]1[CH:10]=[C:11]([CH:17]=[CH:18][CH:19]=1)[CH:12]=[CH:13][C:14]([OH:16])=[O:15])#[N:8]>O>[C:7]([C:9]1[CH:10]=[C:11]([CH2:12][CH2:13][C:14]([OH:16])=[O:15])[CH:17]=[CH:18][CH:19]=1)#[N:8]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 447258693-(3-Cyanophenyl)-2-propenoic acid

Product 1

HCID 138542693-Cyanobenzenepropanoic acidYield 85.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 200 ml of a solution of 20.0 g potassium carbonate in 250 ml water, 15 g of 3-cyanocinnamic acid was added; the resulting mixture was heated until all the acid was in solution. The solution was cooled and filtered and rinsed with water to 250 ml total volume. Then 0.95 g of 10% palladium on carbon was added and the solution was hydrogenated at 8.5 psi for two hours. The reaction mixture was filtered, and then acidified to a pH of about 1 by the dropwise addition of concentrated hydrochloric acid, being careful to avoid too much foaming. The mixture was chilled in an ice bath and filtered to collect the precipitated product acid. The precipitate was rinsed several times with cold water and dried overnight, to give 13 g of the above-identified product as a solid, melting point 95° C.

Workup

  1. temperaturethe resulting mixture was heated until all the acid
  2. temperatureThe solution was cooled
  3. filtrationfiltered
  4. washrinsed with water to 250 ml total volume
  5. additionThen 0.95 g of 10% palladium on carbon was added
  6. filtrationThe reaction mixture was filtered
  7. additionacidified to a pH of about 1 by the dropwise addition of concentrated hydrochloric acid
  8. temperatureThe mixture was chilled in an ice bath
  9. filtrationfiltered
  10. customto collect the precipitated product acid
  11. washThe precipitate was rinsed several times with cold water
  12. customdried overnight

Sources & evidence

ORD record
ord-7cdb4b2ecb504d378ff38549811cb323
Source dataset
uspto-grants-1992_04
Patent number
US05108363

Reaction notes

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