Water → 3-Chloro-5-(trifluoromethoxy)phenylacetic acid

HRID 1990733Notes

Reaction equation

HRID 1990733 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([O:11][C:12]([F:15])([F:14])[F:13])[CH:10]=1)[CH2:5][C:6]#N.[OH2:16].[OH-:17].[K+]>CC(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:5][C:6]([OH:17])=[O:16])[CH:8]=[C:9]([O:11][C:12]([F:15])([F:14])[F:13])[CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 219046503-Chloro-5-(trifluoromethoxy)phenylacetonitrile

Product 1

HCID 219046383-Chloro-5-(trifluoromethoxy)phenylacetic acidYield 76%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 3-chloro-5-trifluoromethoxybenzyl cyanide (6.3 g, 26.7 mmol; see step (ii) above) in 2-propanol (100 mL) was added water (200 mL) and potassium hydroxide (7.5 g, 133.5 mmol). The solution was refluxed for 18 h, cooled to room temperature, and the 2-propanol was removed in vacuo. The aqueous phase was washed with CH2Cl2 (2×) and the washings discarded. The basic aqueous phase was acidified with 2N HCl and extracted with CH2Cl2 (3×). The CH2Cl2 extracts were dried (Na2SO4), filtered and concentrated in vacuo to afford the sub-title compound (5.2 g, 76%) as an oil which was used in the next step without further purification.

Workup

  1. temperatureThe solution was refluxed for 18 h
  2. customthe 2-propanol was removed in vacuo
  3. washThe aqueous phase was washed with CH2Cl2 (2×)
  4. extractionextracted with CH2Cl2 (3×)
  5. dry with materialThe CH2Cl2 extracts were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-176acfbb34ad4d118c399228bfa6a6cf
Source dataset
uspto-grants-2010_01
Patent number
US07645751B2

Reaction notes

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