Reaction #51340

Reaction equation

nitrile

3,5-dichlorophenylacetonitrile

sulfuric acid

H2O

→

white solid

3,5-dichlorophenylacetic acid

Solvents

hexane

Conditions

Workup

1. 1
   Temperatureheated
2. 2
   Temperatureto reflux for 48 hours
3. 3
   Temperaturewarmed
4. 4
   Extractionextracted with 2×200 mL of dichloromethane and 2×200 mL of ethylacetate
5. 5
   Washwashed with saturated aqueous NaHCO3
6. 6
   Filtrationto filter
7. 7
   Extractionwas extracted out with 2×200 mL of dichloromethane
8. 8
   DryingThe combined organics were dried with Na2SO4
9. 9
   Otherthe solvents removed
10. 10
    Otherto yield crude 3,5-dichlorophenylacetic acid as a white solid
11. 11
    Filtrationfiltered

Procedure

The nitrile was added to a mixture of 40 mL of concentrated sulfuric acid and 50 mL H2O and heated to reflux for 48 hours, cooled to room temperature and stirred for 48 hours. The reaction was diluted into 1 L of crushed ice, warmed to toom temperature and extracted with 2×200 mL of dichloromethane and 2×200 mL of ethylacetate. Both sets of organics were combined and washed with saturated aqueous NaHCO3. The NaHCO3 fractions were combined and acidified to pH 1 with 3N HCl. The white solid was too fine to filter and was extracted out with 2×200 mL of dichloromethane. The combined organics were dried with Na2SO4 and the solvents removed at reduced presure to yield crude 3,5-dichlorophenylacetic acid as a white solid. The solid was slurried with hexane and filtered to get 1.75 g of white solid.

Source