3-(3,4-Difluorophenyl)-2-methylprop-2-enoic acid → 3-(3,4-Difluorophenyl)-2-methylpropanoic acid

HRID 377745Notes

Reaction equation

HRID 377745 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][C:13]=1[F:14])[CH:5]=[C:6]([CH3:10])[C:7]([OH:9])=[O:8]>CO.O=[Pt]=O>[F:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][C:13]=1[F:14])[CH2:5][CH:6]([CH3:10])[C:7]([OH:9])=[O:8]

Participants

4

Reactant 1

HCID 539805853-(3,4-Difluorophenyl)-2-methylprop-2-enoic acid

Product 1

HCID 120521423-(3,4-Difluorophenyl)-2-methylpropanoic acid

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

3,4-difluoro-α-methylcinnamic acid (28 g; 0.141 mol), PtO2 (1 g) in MeOH (250 ml) is hydrogenated at 45 p.s.i. until the theoretical uptake is completed. The catalyst is filtered off, and the material is evaporated to one-third of its original volume. A 15% potassium hydroxide solution (10 ml) is added, and the mixture is refluxed for 30 minutes. It is poured into water and extracted with ether (2×100 ml). The aqueous layer is acidified with concentrated HCl and ice, to produce an oil which is extracted into ether. The ether solution is dried over MgSO4, and is evaporated to leave 3,4-difluoro-α-methylhydrocinnamic acid (m.p. 55-56° C.) as a clear oil which crystallizes.

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe material is evaporated to one-third of its original volume
  3. additionA 15% potassium hydroxide solution (10 ml) is added
  4. temperaturethe mixture is refluxed for 30 minutes
  5. additionIt is poured into water
  6. extractionextracted with ether (2×100 ml)
  7. customto produce an oil which
  8. extractionis extracted into ether
  9. dry with materialThe ether solution is dried over MgSO4
  10. customis evaporated

Sources & evidence

ORD record
ord-dc27225919754ec295349bfb17b07274
Source dataset
uspto-grants-2000_02
Patent number
US06028116

Reaction notes

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