Reaction #939045

Reaction equation

Ethyl 4-nitrobenzoate

potassium cyanide

DMSO

→

ethyl 3-cyano-4-hydroxybenzoate

Conditions

Workup

1. 1
   Temperaturecooled to room temperature
2. 2
   workup.DISTILLATIONDMSO was distilled off
3. 3
   workup.ADDITIONto the residue was added ice-water (200 mL)
4. 4
   WashThe aqueous residue was washed with ethyl acetate (100 mL)
5. 5
   workup.ADDITIONTo the mixture was added conc. hydrochloric acid
6. 6
   ExtractionThe mixture was then extracted with ethyl acetate (200 mL)
7. 7
   Washwashed with aqueous saturated brine (50 mL)
8. 8
   Dryingdried over anhydrous sodium sulfate
9. 9
   workup.DISTILLATIONto distill the solvent off

Procedure

Ethyl 4-nitrobenzoate (50.0 g, 256 mmol) and potassium cyanide (51.2 g, 786 mmol) were added to DMSO (380 mL), stirred at 100° C. for 4 hours, and cooled to room temperature. DMSO was distilled off, and to the residue was added ice-water (200 mL). The aqueous residue was washed with ethyl acetate (100 mL). To the mixture was added conc. hydrochloric acid, to change the pH of the mixture to 1. The mixture was then extracted with ethyl acetate (200 mL), washed with aqueous saturated brine (50 mL), dried over anhydrous sodium sulfate, and placed under reduced pressure to distill the solvent off. There was obtained 51.4 g of ethyl 3-cyano-4-hydroxybenzoate as a crude product.

Source