Sodium Hydroxide → 2-Cyano-3-phenylpropionic acid

HRID 1607389

Reaction equation

HRID 1607389 reaction equation
C([O:3][C:4](=[O:15])[CH:5]([C:13]#[N:14])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)C.[OH-].[Na+]>C(O)C>[C:13]([CH:5]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:4]([OH:15])=[O:3])#[N:14]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 228103Ethyl 2-cyano-3-phenylpropanoate

Product 1

HCID 2200552-Cyano-3-phenylpropionic acidYield 92.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 406 mg of 2-cyano-3-phenylpropionic acid ethyl ester in 10 ml of ethanol were added 1.1 ml of a 2N-aqueous sodium hydroxide solution, and then the mixture was stirred for 16 hours at room temperature. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in water and washed with diethyl ether. The aqueous solution was adjusted to a pH of 2 by adding a 2N-hydrochloric acid and extracted with diethyl ether. The ethereal layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain 324 mg of 2-cyano-3-phenylpropionic acid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in water
  3. washwashed with diethyl ether
  4. additionby adding a 2N-hydrochloric acid
  5. extractionextracted with diethyl ether
  6. washThe ethereal layer was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ee2bf308e7aa4033b7e3d88a2e8bd8cb
Source dataset
uspto-grants-1989_09
Patent number
US04863904

Linked notes

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