8-(4-Fluoro-3-methylphenyl)oct-7-enoic acid → 8-(4-Fluoro-3-methylphenyl)octanoic acid

HRID 885520Notes

Reaction equation

HRID 885520 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[CH:4][C:3]=1[CH3:18]>CO.[Pd]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[CH:4][C:3]=1[CH3:18]

Participants

4

Reactant 1

HCID 686422388-(4-Fluoro-3-methylphenyl)oct-7-enoic acid

Product 1

HCID 595125948-(4-Fluoro-3-methylphenyl)octanoic acidYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 8-(4-fluoro-3-methylphenyl)oct-7-enoic acid (0.976 g, 3.899 mmol) in 30 mL of MeOH, was added 10% Pd on C (0.195 g). After stirred at room temperature under H2 (1 atm) for 63 h, the reaction mixture was filtered through a pad of Celite and washed with ethyl acetate. The filtrate was concentrated under reduced pressure. The residue was used directly in the next step without further purification (0.938 g, 95% yield). LC-MS: tR=10.1 min, m/z 253 (M+H)+.

Workup

  1. filtrationthe reaction mixture was filtered through a pad of Celite
  2. washwashed with ethyl acetate
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customThe residue was used directly in the next step without further purification (0.938 g, 95% yield)

Sources & evidence

ORD record
ord-3788ef694eda47b4a01eb2dc381bf708
Source dataset
uspto-grants-2012_08
Patent number
US08242174B2

Reaction notes

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