3-(3,5-Difluorophenyl)acrylic acid → 3-(3,5-Difluorophenyl)propionic acid

HRID 1193597Notes

Reaction equation

HRID 1193597 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]([OH:13])=[O:12])[CH:5]=[C:6]([F:8])[CH:7]=1.[H][H]>O1CCCC1.[Pd].C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][C:11]([OH:13])=[O:12])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

6

Reactant 2

HCID 5228103-(3,5-Difluorophenyl)acrylic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 36694983-(3,5-Difluorophenyl)propionic acidYield 99%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-(3,5-difluorophenyl)propenoic acid (0.0435 mol) in tetrahydrofuran (100 ml) and a slurry of 10% palladium on carbon (1.5 g) in ethyl acetate were shaken together under 50 psi hydrogen for 4 hours. The mixture was filtered and concentrated to yield 8 g (99%) of a yellow oil.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-b3e6f6ac2ae54fdeac4eaf42c00d5311
Source dataset
uspto-grants-1989_03
Patent number
US04810811

Reaction notes

Loading…