3-(4-Fluorobenzoyl)propionic acid → 4-(p-Fluorophenyl)butyric acid

HRID 362841Notes

Reaction equation

HRID 362841 reaction equation
[F:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=O)=[CH:4][CH:3]=1>[Pd].C(O)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:13][CH:14]=1

Participants

4

Reactant 1

HCID 1013593-(4-Fluorobenzoyl)propionic acid

Product 1

HCID 685244-(p-Fluorophenyl)butyric acidYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 3-(4-fluorobenzoyl)propanoic acid (42.3 g, 0.22 mol) and 10% Palladium on carbon (3 g) in acetic acid (250 mL) was hydrogenated at 50 psi and 25° C. for 6 h. The mixture was filtered and concentrated in vacuo. The residue was distilled at 0.02 mm Hg and the product crystallized to give 4-(4-fluorophenyl)butyric acid as a white solid (97%). m.p., 44°-46.2° C. (lit. J. Am. Chem. Soc. 89, 386, 1967; m.p., 45.5°-46.5° C.).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated in vacuo
  3. distillationThe residue was distilled at 0.02 mm Hg
  4. customthe product crystallized

Sources & evidence

ORD record
ord-12a675fc48b94d4c90191a71c2200b3f
Source dataset
uspto-grants-1999_02
Patent number
US05872118

Reaction notes

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