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

Temperature

100 °C

3-(3-Methylphenyl)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 2.5 hr. The reaction mixture was concentrated, and the residue was washed with water. The obtained colorless oil was dissolved in tetrahydrofuran (60 ml), 1M diisobutylaluminum hydride/toluene solution (38 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. The mixture was extracted with ethyl acetate, washed with 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 (2.45 g) as a colorless oil.

1. concentrationThe reaction mixture was concentrated
2. washthe residue was washed with water
3. dissolutionThe obtained colorless oil was dissolved in tetrahydrofuran (60 ml)
4. addition1M diisobutylaluminum hydride/toluene solution (38 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. extractionThe mixture was extracted with ethyl acetate
10. washwashed with 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-defb5d3ad82d49b387bf43c82831bc0a

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08129361B2