Hydrochloric Acid → 1-[4-(Hydroxymethyl)phenyl]butan-1-ol

4-(1-Hydroxybutyl)benzaldehyde (4.51 g, 25.3 mmol) was dissolved in a mixture of methanol (10 mL) and tetrahydrofuran (20 mL), and sodium borohydride (0.479 g, 12.7 mmol) was added with stirring under ice-cooling. The mixture was stirred at the same temperature for 1.5 hr. Water and 1N hydrochloric acid were added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=30:70-80:20) to give the title compound (4.32 g, yield 95%) as a colorless oil.

1. additionwas added
2. temperaturecooling
3. stirringThe mixture was stirred at the same temperature for 1.5 hr
4. extractionthe mixture was extracted with ethyl acetate
5. washThe extract was washed with saturated brine
6. dry with materialdried over anhydrous magnesium sulfate
7. concentrationconcentrated under reduced pressure
8. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=30:70-80:20)

ORD record

ord-55e747515c7e41178baee90aae981607

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07585880B2