3-(2,4-Difluorophenyl)acrylic Acid → 3-(2,4-difluorophenyl)propanoic Acid

HRID 1954862Notes

Reaction equation

HRID 1954862 reaction equation
[F:1][C:2]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:3]=1[CH:4]=[CH:5][C:6]([OH:8])=[O:7].[H][H]>C(O)C.O.[Pt]=O>[F:1][C:2]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:3]=1[CH2:4][CH2:5][C:6]([OH:8])=[O:7]

Participants

5

Reactant 2

HCID 6035023-(2,4-Difluorophenyl)acrylic AcidHCID 178418361HCID 178418361, compound

Product 1

HCID 49863953-(2,4-difluorophenyl)propanoic AcidYield 99.7%

Reagents, catalysts & solvents 2

HCID 86587499Platinum oxide monohydrateCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2,4-difluorocinnamic acid (30.0 g, 0.16 mol, Aldrich) and platinum oxide hydrate (0.5 g, EM Scientific) in 95% ethanol (140 mL) was placed on Parr hydrogenation apparatus. After the appropriate amount of hydrogen was taken up, the catalyst was filtered and the filtrate was concentrated in vacuo to give 29.7 g (98%) of 3-(2,4difluorophenyl)propanoic acid as a white solid. Recrystallization of 1.0 g from acetonitrile; water mixtures gave 0.61 g of 3-(2,4-difluorophenyl)propanoic acid as a white solid: mp 104-106° C.; NMR (DMSO-d6); d 12.2 (br, 1H), 6.98-7.40 (m, 3H), 2.81 (t, 2H), 2.51 (t, 2H).

Workup

  1. filtrationthe catalyst was filtered
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-f27e5bf25d9c4ce1b521b6b3b4e62661
Source dataset
uspto-grants-2000_09
Patent number
US06124284

Reaction notes

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