Sodium Hydroxide → 3-Cyano-4-isobutylbenzoic acid

HRID 851865Notes

Reaction equation

HRID 851865 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1OCC(C)C)[C:6]([O:8]CC)=[O:7])#[N:2].[OH-].[Na+]>C(O)C.C1COCC1>[C:1]([C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[CH2:1][CH:3]([CH3:4])[CH3:13])[C:6]([OH:8])=[O:7])#[N:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 23023859HCID 23023859, compound

Product 1

HCID 222281753-Cyano-4-isobutylbenzoic acidYield 212.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
30 °C

Procedure

Ethyl 3-cyano-4-isobutyloxybenzoate (20.0 g, 80.9 mmol) was dissolved in a mixture of ethanol (100 mL) and THF (100 mL). Aqueous 2M sodium hydroxide (45 mL, 90.0 mmol) was added to the resulting solution, and the mixture was stirred at 30° C. for 4 hours. The solvent was distilled off under reduced pressure. Water (100 mL) was added to the residue and further aqueous 2M hydrochloric acid to obtain an aqueous mixture of pH 1. The precipitated crystalline product was collected by filtration, washed with water (200 mL×2), and dried in air, to give 17.5 g (yield 99%) of the desired compound in the form of a white crystalline product.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. additionWater (100 mL) was added to the residue and further aqueous 2M hydrochloric acid
  3. customto obtain
  4. additionan aqueous mixture of pH 1
  5. filtrationThe precipitated crystalline product was collected by filtration
  6. washwashed with water (200 mL×2)
  7. customdried in air

Sources & evidence

ORD record
ord-94383e7190154706ae5b27b85ba45317
Source dataset
uspto-grants-2007_08
Patent number
US07253154B2

Reaction notes

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