Sulfuric Acid → 2-Propen-1-ol, 3-(4-methylphenyl)-, (2E)-

Temperature

100 °C

3-(4-Methylphenyl)acrylic acid (5.0 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 white solid was dissolved in tetrahydrofuran (120 ml), 1M diisobutylaluminum hydride/toluene solution (67 ml) was added dropwise at −78° C., and the mixture was stirred as it was at −78° C. for 2 hr. Saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was stirred at room temperature. Aluminum salt was collected by filtration through celite, extracted with methylene chloride, 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 (3.84 g) as a white powder.

1. concentrationThe reaction mixture was concentrated
2. washthe residue was washed with water
3. dissolutionThe obtained white solid was dissolved in tetrahydrofuran (120 ml)
4. addition1M diisobutylaluminum hydride/toluene solution (67 ml) was added dropwise at −78° C.
5. stirringthe mixture was stirred as it
6. waitwas at −78° C. for 2 hr
7. additionSaturated aqueous ammonium chloride solution was added to the reaction mixture
8. stirringthe mixture was stirred at room temperature
9. filtrationAluminum salt was collected by filtration through celite
10. extractionextracted with methylene chloride
11. washwashed with saturated brine
12. dry with materialdried over anhydrous sodium sulfate
13. customThe solvent was evaporated under reduced pressure
14. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate)

ORD record

ord-61a4d1237cab4726bcb87b56a88a9401

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08129361B2