Water → 2-(3,5-Dichlorophenyl)acetic acid

HRID 2271125Notes

Reaction equation

HRID 2271125 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]#N)[CH:5]=[C:6]([Cl:8])[CH:7]=1.S(=O)(=O)(O)[OH:13].[OH2:17]>CCCCCC>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:13])=[O:17])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 126899782-(3,5-Dichlorophenyl)acetonitrile

Product 1

HCID 64524872-(3,5-Dichlorophenyl)acetic acid

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

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.

Workup

  1. temperatureheated
  2. temperatureto reflux for 48 hours
  3. temperaturewarmed
  4. extractionextracted with 2×200 mL of dichloromethane and 2×200 mL of ethylacetate
  5. washwashed with saturated aqueous NaHCO3
  6. filtrationto filter
  7. extractionwas extracted out with 2×200 mL of dichloromethane
  8. dry with materialThe combined organics were dried with Na2SO4
  9. customthe solvents removed
  10. customto yield crude 3,5-dichlorophenylacetic acid as a white solid
  11. filtrationfiltered

Sources & evidence

ORD record
ord-622154f19492499c891ff206401764ad
Source dataset
uspto-grants-2001_12
Patent number
US06333351B1

Reaction notes

Loading…