Reaction #1340555

Reaction equation

3-(trifluoromethyl) cinnamic acid

ethanol

→

captioned compound

3-(3-trifluoromethylphenyl)-propionic acid methyl ester

Conditions

Workup

1. 1
   OtherPalladium/carbon was separated by filtration
2. 2
   Concentrationthe filtrate was concentrated under reduced pressure
3. 3
   workup.ADDITION20 ml of methanol and 4 drops of concentrated sulfuric acid were added
4. 4
   workup.STIRRINGthe mixture was stirred at 60° C. for 2 hours
5. 5
   workup.WAITleft
6. 6
   Temperatureto cool down
7. 7
   ConcentrationAfter concentration under reduced pressure, 20 ml of a saturated sodium bicarbonate aqueous solution
8. 8
   workup.ADDITIONwas added
9. 9
   Extractionthe resultant was extracted with 20 ml of dichloromethane
10. 10
    DryingThe extract was dried with anhydrous sodium sulfate
11. 11
    Concentrationconcentrated under reduced pressure

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.

Source