Ethanol → 1-(4-Aminophenyl)-2-propanol

A mixture of 1-(4-nitrophenyl)-2-propanol (Schadt, F. J. Am. Chem. Soc., 1978, 100, 228., 2.2 g, 12.3 mmol), iron powder (3.3 g, 59.1 mmol), ammonium chloride (370 mg, 6.9 mmol), ethanol (48 mL) and water (24 mL) was heated at reflux temperature for 2 h. The mixture was cooled and filtered through a pad of Celite. The filtrate was concentrated. The residue was diluted with ethyl acetate (200 mL) and washed with water (2×100 mL). The organic layer was dried (MgSO4), and concentrated. Purification by flash column chromatography on silica gel eluting with hexane/ethyl acetate (1:1) to afford 1.45 g (78%) of the title compound as a yellow oil: 1H-NMR (CDCl3) δ 7.00 (2H, d, J=8.6 Hz), 6.64 (2H, d, J=8.8 Hz), 3.99-3.89 (1H, m), 3.60 (2H, br s), 2.72-2.52 (2H, m), 1.22 (3H, d, J=6.2 Hz).

1. temperaturewas heated
2. temperatureat reflux temperature for 2 h
3. temperatureThe mixture was cooled
4. filtrationfiltered through a pad of Celite
5. concentrationThe filtrate was concentrated
6. additionThe residue was diluted with ethyl acetate (200 mL)
7. washwashed with water (2×100 mL)
8. dry with materialThe organic layer was dried (MgSO4)
9. concentrationconcentrated
10. customPurification by flash column chromatography on silica gel eluting with hexane/ethyl acetate (1:1)

ORD-Eintrag

ord-4339b9fc705e423eb61b9ed02d3edece

Quelldatensatz

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07928119B2