4-Fluoro-2-methylcinnamic acid → 3-(4-Fluoro-2-methylphenyl)propanoic acid

HRID 717096Notes

Reaction equation

HRID 717096 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([OH:12])=[O:11])=[C:4]([CH3:13])[CH:3]=1>CCO.O=[Pt]=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[C:4]([CH3:13])[CH:3]=1

Participants

4

Reactant 1

HCID 547757764-Fluoro-2-methylcinnamic acid

Product 1

HCID 109761163-(4-Fluoro-2-methylphenyl)propanoic acidYield 77%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

To a solution of (E)-3-(4-fluoro-2-methylphenyl)acrylic acid (13 g, 72.22 mmol) in EtOH (250 mL) was added PtO2 (250 mg) and then hydrogenated at 30 psi for 3 h. The reaction mixture was filtered on a Celite® pad, washed with MeOH (100 mL), and the filtrate was concentrated, washed with diethyl ether (20 mL), n-pentane (50 mL) and dried in vacuo to give 3-(4-fluoro-2-methylphenyl)propanoic acid as an off-white solid (10 g, 77%).

Workup

  1. filtrationThe reaction mixture was filtered on a Celite® pad
  2. washwashed with MeOH (100 mL)
  3. concentrationthe filtrate was concentrated
  4. washwashed with diethyl ether (20 mL), n-pentane (50 mL)
  5. customdried in vacuo

Sources & evidence

ORD record
ord-79d985e59f7647fb95001a9945841217
Source dataset
uspto-grants-2015_11
Patent number
US09193689B2

Reaction notes

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