HCID 53980585, compound → 3-(3,4-Difluorophenyl)-2-methylpropanoic acid

HRID 1955708Notes

Reaction equation

HRID 1955708 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 53980585HCID 53980585, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

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

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe material evaporated to one-third its volume
  3. additionA 15% potassium hydroxide solution (10 ml) is added
  4. temperaturethe mixture refluxed for 30 minutes when it
  5. additionis poured into water
  6. extractionextracted with ether (2×100 ml)
  7. extractionThe oil which comes out is extracted into ether
  8. dry with materialthe ether solution dried over MgSO4
  9. customevaporated
  10. customto leave a clear oil which
  11. customcrystallizes

Sources & evidence

ORD record
ord-9df69403c5234c60ba435e0898ae21d6
Source dataset
uspto-grants-1998_07
Patent number
US05776962

Reaction notes

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