Sodium Hydroxide → p-Propionylbenzoic acid

HRID 218079Notes

Reaction equation

HRID 218079 reaction equation
[CH3:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9]C(C#N)=[CH:7][CH:6]=1)=[O:4].[OH-:13].[Na+].[O:15]1[CH2:20][CH2:19]OCC1>O>[C:3]([C:5]1[CH:10]=[CH:9][C:19]([C:20]([OH:15])=[O:13])=[CH:7][CH:6]=1)(=[O:4])[CH2:2][CH3:1]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 107732464-Propanoylbenzonitrile

Product 1

HCID 20202p-Propionylbenzoic acidYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Cyanopropiophenone (4.67 g, 29.3 mmol) was refluxed with 2N NaOH (90 mL, 180 mmol) and dioxane (90 mL) at 95° C. overnight. The mixture was diluted with water (150 mL), washed with ether (75 mL), acidified to pH 2 with concentrated HCl, and extracted with ether (3×75 mL). The organic phase was washed with saturated aqueous NaCl (3×75 mL), dried, and concentrated to give a yellow solid (5.12 g, 98%).

Workup

  1. washwashed with ether (75 mL)
  2. extractionextracted with ether (3×75 mL)
  3. washThe organic phase was washed with saturated aqueous NaCl (3×75 mL)
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3c189b78ff594304b308295ce08429d0
Source dataset
uspto-grants-2012_06
Patent number
US08198283B2

Reaction notes

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