Reaction #1340556

Reaction equation

hydrochloric acid

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

diisopropyl aluminum hydride

ammonium chloride

→

captioned compound

Yield 101.5%

3-(3-trifluoromethylphenyl)propanal

Yield 101.5%

Solvents

water

dichloromethane

hexane

Conditions

Workup

1. 1
   workup.STIRRINGthe mixture was stirred
2. 2
   Otherthe resultant was separated into an aqueous layer
3. 3
   ExtractionThe aqueous layer was extracted with dichloromethane
4. 4
   Dryingdried over anhydrous sodium sulfate
5. 5
   Concentrationconcentrated under reduced pressure

Procedure

2.40 g of 3-(3-trifluoromethylphenyl)-propionic acid methyl ester synthesized in Step 1 was dissolved in 20 ml of dry dichloromethane. 13 ml of diisopropyl aluminum hydride solution (0.91 M) in hexane was dropped over 5 minutes at −78° C. under an argon atmosphere, and the mixture was stirred at the same temperature for 40 minutes. 50 ml of a saturated ammonium chloride aqueous solution was dropped, and then the mixture was stirred and the temperature was raised to room temperature. 20 ml of water and 5 ml of concentrated hydrochloric acid were added, and the resultant was separated into an aqueous layer and an organic layer. The aqueous layer was extracted with dichloromethane, and the extract was combined with the separated organic layer, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to afford 2.12 g of the captioned compound as an oil.

Source