Ethanol → Ethyl 3-(4-fluorophenyl)butyrate

HRID 362856Notes

Reaction equation

HRID 362856 reaction equation
[F:1][C:2]1[CH:14]=[CH:13][C:5]([CH:6]=[CH:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:4][CH:3]=1.[CH2:15](O)C>[Pd]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]([CH3:15])[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 367200Ethyl 3-(4-fluorophenyl)prop-2-enoate

Product 1

HCID 11160124Ethyl 3-(4-fluorophenyl)butyrateYield 97%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of ethyl 4-fluorocinnamate (47.5 g, 0.228 mol) and 10% palladium on carbon (0.85 g, Aldrich) in 95% ethanol was shaken in a Parr hydrogenator under 2-3 atm of H2 pressure for 1 h. The mixture was filtered and concentrated by spin evaporation in vacuo. Fractional distillation gave 46.5 g (97%) of ethyl 3-(4-fluorophenyl)butyrate as a clear oil, b.p., 122°-128° C.: c) Preparation of 3-(4-Fluorophenyl)butanoic Acid.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated by spin evaporation in vacuo
  3. distillationFractional distillation

Sources & evidence

ORD record
ord-387b42f1c016472998785cedc9bde248
Source dataset
uspto-grants-1999_02
Patent number
US05872118

Reaction notes

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