Sodium Hydroxide → 3-(4-Cyano-3-hydroxy-phenyl)-propionic acid

HRID 2215281Notes

Reaction equation

HRID 2215281 reaction equation
C([O:3][C:4](=[O:16])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[C:9]([OH:15])[CH:8]=1)C.[OH-].[Na+]>C(O)C.O>[C:13]([C:10]1[CH:11]=[CH:12][C:7]([CH2:6][CH2:5][C:4]([OH:16])=[O:3])=[CH:8][C:9]=1[OH:15])#[N:14]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 9834402Ethyl 3-(4-cyano-3-hydroxyphenyl)propanoate

Product 1

HCID 219502013-(4-Cyano-3-hydroxy-phenyl)-propionic acidYield 98.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 3-(4-Cyano-3-hydroxy-phenyl)-propionic acid ethyl ester (2.2 g, 10 mmol) in ethanol (10 mL) and water (40 mL) was treated with aqueous sodium hydroxide solution (2.5 M, 44 mL) at room temperature overnight. The solvent was removed under vacuum and the residue was dissolved in water (150 mL). The pH of the aqueous solution was adjusted to 2–4 by the addition of 3N HCl (aqueous) and the precipitate was then filtered and washed with water to give the title compound as white solid (1.88 g, 0.98 mmol, 98.4% yield). ESMS m/z: 192 [M+H]+.

Workup

  1. customThe solvent was removed under vacuum
  2. dissolutionthe residue was dissolved in water (150 mL)
  3. additionThe pH of the aqueous solution was adjusted to 2–4 by the addition of 3N HCl (aqueous)
  4. filtrationthe precipitate was then filtered
  5. washwashed with water

Sources & evidence

ORD record
ord-bc4df98abb674dae8f045995e3eb0883
Source dataset
uspto-grants-2006_09
Patent number
US07109238B2

Reaction notes

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