Hydrochloric Acid → 3-(4-Methylsulfanyl-phenyl)-propan-1-OL

3-(4-Methylsulfanylphenyl)propionic acid (1.00 g) was dissolved in tetrahydrofuran (20 ml), and a tetrahydrofuran-borane.tetrahydrofuran solution (1 mol/l, 6.42 ml) was added dropwise to the mixture under ice-cooling. The mixture was stirred under ice-cooling for 30 min, and further at room temperature for 1 hr. Water was added to the reaction mixture, and 1 mol/l aqueous hydrochloric acid solution was added. The mixture was extracted with ethyl acetate, washed with water, saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography to give the object product (940 mg) as a colorless oil.

1. temperaturecooling
2. temperaturecooling for 30 min
3. additionwas added
4. extractionThe mixture was extracted with ethyl acetate
5. washwashed with water, saturated aqueous sodium hydrogen carbonate solution and saturated brine
6. dry with materialdried over anhydrous magnesium sulfate
7. customThe solvent was evaporated under reduced pressure
8. customThe residue was purified by silica gel chromatography

ORD record

ord-dc64a8753add475fb3266aac59b62ac0

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08129361B2