Reaction #939047

Reaction equation

Ethyl 3-cyano-4-isobutyloxybenzoate

sodium hydroxide

→

desired compound

3-Cyano-4-isobutylbenzoic acid

Solvents

ethanol

THF

Conditions

Workup

1. 1
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure
2. 2
   workup.ADDITIONWater (100 mL) was added to the residue and further aqueous 2M hydrochloric acid
3. 3
   Otherto obtain
4. 4
   workup.ADDITIONan aqueous mixture of pH 1
5. 5
   FiltrationThe precipitated crystalline product was collected by filtration
6. 6
   Washwashed with water (200 mL×2)
7. 7
   Otherdried in air

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.

Source