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

A mixture of 1-(4-nitrophenyl)-2-propanol (Schadt, F. L.; et al. 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 record

ord-41a1df99cb0d484da5369b5c9fd19ef1

Source dataset

uspto-grants-2006_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07141580B2