Sulfuric Acid → 3-(3-Trifluoromethylphenyl)-2-propene-1-ol

Temperature

100 °C

3-(3-Trifluoromethylphenyl)acrylic acid (3.0 g) was dissolved in methanol (30 ml), concentrated sulfuric acid (0.5 ml) was added, and the mixture was stirred at 100° C. for 5.5 hr. The reaction mixture was concentrated, and the residue was washed with water. The obtained white powder was dissolved in tetrahydrofuran (40 ml), 1M diisobutylaluminum hydride/toluene solution (26 ml) was added dropwise at −78° C., and the mixture was stirred as it was at −78° C. for 2 hr. Saturated Rochelle salt water, water and ethyl acetate were added to the reaction mixture, and the mixture was stirred at room temperature, extracted with ethyl acetate, washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate) to give the object product (2.0 g) as a colorless oil.

1. concentrationThe reaction mixture was concentrated
2. washthe residue was washed with water
3. dissolutionThe obtained white powder was dissolved in tetrahydrofuran (40 ml)
4. addition1M diisobutylaluminum hydride/toluene solution (26 ml) was added dropwise at −78° C.
5. stirringthe mixture was stirred as it
6. waitwas at −78° C. for 2 hr
7. additionSaturated Rochelle salt water, water and ethyl acetate were added to the reaction mixture
8. stirringthe mixture was stirred at room temperature
9. extractionextracted with ethyl acetate
10. washwashed with water and saturated brine
11. dry with materialdried over anhydrous sodium sulfate
12. customThe solvent was evaporated under reduced pressure
13. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate)

ORD record

ord-dbb26838102d4d50b320c9474bc7510f

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08129361B2