Potassium Hydroxide → 4-(Difluoromethyl)benzoic acid

HRID 241444Notes

Reaction equation

HRID 241444 reaction equation
[F:1][CH:2]([F:13])[C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9]C)=[O:8])=[CH:5][CH:4]=1.[OH-].[K+]>CO>[F:1][CH:2]([F:13])[C:3]1[CH:4]=[CH:5][C:6]([C:7]([OH:9])=[O:8])=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 22262108Methyl 4-(difluoromethyl)benzoate

Product 1

HCID 207393254-(Difluoromethyl)benzoic acidYield 96.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dissolve methyl 4-(difluoromethyl)benzoate (2.855 g, 15.336 mmol) in MeOH (30 mL). Add potassium hydroxide (8.41 mL 2 equivalents, 30.7 mmol), and stir the mixture for 16 hours. Concentrate the reaction mixture under reduced pressure, and add EtOAc (100 mL) and 1 N HCl (50 mL). Stir for 30 minutes. Separate the layers. Dry the organics over Na2SO4; filter; collect the filtrate; and concentrate the filtrate under reduced pressure to give the titled compound as a white solid (2.541 g, 96% yield). 1H NMR (399.83 MHz, d6-DMSO) δ 13.29-13.28 (m, 1H), 8.04 (d, J=7.8 Hz, 2H), 7.67 (d, J=8.0 Hz, 2H), 7.24-6.97 (t, J=55.6, 1H).

Workup

  1. concentrationConcentrate the reaction mixture under reduced pressure
  2. additionadd EtOAc (100 mL) and 1 N HCl (50 mL)
  3. customSeparate the layers
  4. dry with materialDry the organics over Na2SO4
  5. filtrationfilter
  6. customcollect the filtrate
  7. concentrationand concentrate the filtrate under reduced pressure

Sources & evidence

ORD record
ord-d6d72ec838ff4ff1be997c257bbd8761
Source dataset
uspto-grants-2014_02
Patent number
US08648200B2

Reaction notes

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