Potassium Hydroxide → 3-Cyano-4-hydroxybenzoic acid

HRID 1166720Notes

Reaction equation

HRID 1166720 reaction equation
C[O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([C:11]#[N:12])[CH:5]=1.[OH-].[K+]>C1COCC1>[C:11]([C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][C:7]=1[OH:10])[C:3]([OH:13])=[O:2])#[N:12]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 11769089Methyl 3-cyano-4-hydroxybenzoate

Product 1

HCID 111374633-Cyano-4-hydroxybenzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl-3-cyano-4-hydroxybenzoate (2.71 g, 15.3 mmol) was dissolved in 50 mL of THF. The solution was chilled in an ice bath, and 2.0M potassium hydroxide (17 mL, 34 mmol) was added dropwise. The resulting mixture was stirred at room temperature overnight. TLC indicated complete reaction. The THF was removed by rotary evaporation. The aqueous residue was acidified with aqueous trifluoroacetic acid and purified by reverse-phase HPLC (C-18, 0.1% TFA in water and acetonitrile). 3-Cyano-4-hydroxybenzoic acid was obtained as a white powder (2.1 g, 84%) after lyophilization.

Workup

  1. temperatureThe solution was chilled in an ice bath
  2. customreaction
  3. customThe THF was removed by rotary evaporation
  4. custompurified by reverse-phase HPLC (C-18, 0.1% TFA in water and acetonitrile)

Sources & evidence

ORD record
ord-5200c5555a92474eb9e4c3bdd5e97488
Source dataset
uspto-grants-2003_09
Patent number
US06613942B1

Reaction notes

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