Oxygen → Benzenepropanoic acid, α-methyl-4-(trifluoromethyl)-, ethyl ester

HRID 1500234Notes

Reaction equation

HRID 1500234 reaction equation
[CH3:1]/[C:2](=[CH:8]\[C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1)/[C:3]([O:5][CH2:6][CH3:7])=[O:4].O=O>[Pd].CO>[CH3:1][CH:2]([CH2:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]([F:16])([F:18])[F:17])=[CH:13][CH:14]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

5

Reactant 2

HCID 977OxygenHCID 102180854HCID 102180854, compound

Product 1

HCID 90111382Benzenepropanoic acid, α-methyl-4-(trifluoromethyl)-, ethyl esterYield 91.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

Dissolve ethyl(E)-2-methyl-3-[4-(trifluoromethyl)phenyl]prop-2-enoate (2.58 g, 10 mmol) in a suspension of 10 wt % Pd—C (258 mg)/MeOH (20 mL) in an RBF under nitrogen, as exposure of Pd—C to oxygen can lead to fire. Carefully purge the flask with hydrogen and stir the resulting mixture under hydrogen (1 Atm) for 16 h. Purge the flask nitrogen and degas the solvent to remove all hydrogen before exposing to air. Filter the suspension through a pad of celite. Concentrate the filtrate to give the title compound (2.39 g).

Workup

  1. customCarefully purge the flask with hydrogen
  2. customPurge the flask nitrogen
  3. customdegas the solvent
  4. customto remove all hydrogen
  5. filtrationFilter the suspension through a pad of celite
  6. concentrationConcentrate the filtrate

Sources & evidence

ORD record
ord-c2290072995c492a97beb5903e224760
Source dataset
uspto-grants-2015_12
Patent number
US09206139B2

Reaction notes

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