Ethanol → Methyl 3-[3-(trifluoromethyl)phenyl]propanoate

HRID 1253373Notes

Reaction equation

HRID 1253373 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][CH:13]=1)[CH:6]=[CH:7][C:8]([OH:10])=[O:9].[CH2:16](O)C>[Pd]>[CH3:16][O:9][C:8](=[O:10])[CH2:7][CH2:6][C:5]1[CH:11]=[CH:12][CH:13]=[C:3]([C:2]([F:14])([F:15])[F:1])[CH:4]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 855273-Trifluoromethylcinnamic acid

Product 1

HCID 53230361Methyl 3-[3-(trifluoromethyl)phenyl]propanoate

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of 2.20 g of 3-(trifluoromethyl) cinnamic acid, 166 mg of palladium/carbon (10%, wet), and 40 ml of ethanol was stirred overnight under a hydrogen atmosphere at 1 atm. Palladium/carbon was separated by filtration, and the filtrate was concentrated under reduced pressure. 20 ml of methanol and 4 drops of concentrated sulfuric acid were added and the mixture was stirred at 60° C. for 2 hours, and then left to cool down. After concentration under reduced pressure, 20 ml of a saturated sodium bicarbonate aqueous solution was added, and the resultant was extracted with 20 ml of dichloromethane. The extract was dried with anhydrous sodium sulfate and then concentrated under reduced pressure to afford 2.40 g of the captioned compound as an oil.

Workup

  1. customPalladium/carbon was separated by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. addition20 ml of methanol and 4 drops of concentrated sulfuric acid were added
  4. stirringthe mixture was stirred at 60° C. for 2 hours
  5. waitleft
  6. temperatureto cool down
  7. concentrationAfter concentration under reduced pressure, 20 ml of a saturated sodium bicarbonate aqueous solution
  8. additionwas added
  9. extractionthe resultant was extracted with 20 ml of dichloromethane
  10. dry with materialThe extract was dried with anhydrous sodium sulfate
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-632fe13c58be4ec886ff11dd65f31167
Source dataset
uspto-grants-2013_06
Patent number
US08454978B2

Reaction notes

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