Sulfuric Acid → 4-(3-Fluorophenyl)butanoic acid

HRID 13688Notes

Reaction equation

HRID 13688 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH2:10][C:11]([OH:13])=[O:12])[CH:5]=[CH:6][CH:7]=1.S(=O)(=O)(O)O>[Pd].O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 537648234-(3-Fluoro-phenyl)-but-3-enoic acid

Product 1

HCID 149151134-(3-Fluorophenyl)butanoic acidYield 101.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Hydrogenate a mixture of 4-(3-fluoro-phenyl)-but-3-enoic acid (22 g, 122 mmol), concentrated sulfuric acid (24 ml), and 5% palladium on carbon (3.58 g) in tetrahydrofuran (470 ml) at 60 psi at room temperature overnight. After filtration of the catalyst, remove most of the tetrahydrofuran by rotary evaporation, dilute the residue with ether, wash with water (2×), dry over anhydrous sodium sulfate, filter, and concentrate to obtain the title compound (22.50 g, 100%). NMR (400 MHz, CDCl3): δ 1.98 (m, 2H), 2.38 (t, 2H), 2.65 (t, 2H), 6.88 (m, 2H), 6.96 (d, 1H), 7.23 (m, 1H).

Workup

  1. filtrationAfter filtration of the catalyst
  2. customremove most of the tetrahydrofuran by rotary evaporation
  3. additiondilute the residue with ether
  4. washwash with water (2×)
  5. dry with materialdry over anhydrous sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-daa45542a9834ddab492c34d5204fee0
Source dataset
uspto-grants-2010_06
Patent number
US07728150B2

Reaction notes

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