Formaldehyde → 2-(2-Nitrophenyl)propan-1-ol

1-Ethyl-2-nitrobenzene (13.5 mL, 100 mmol) was dissolved in dimethylsulfoxide (100 mL). Paraformaldehyde (4.50 g, 150 mmol) and KOtBu (2.81 g, 25 mmol) in t-butyl alcohol (30 mL) were added and the mixture was stirred at room temperature for 3 h. The solution was washed with a molar solution of HCl (25 mL), followed by brine (3×100 mL). All the aqueous layers were combined and extracted with ethyl acetate (3×100 mL). The organic portion was dried (MgSO4), filtered and the solvent was removed in vacuo. The crude product was purified on a silica gel column. Elution of the column with 20-30% ethyl acetate in hexanes gave 16.12 g (89 mmol, 89% yield) of 2-(2-nitrophenyl)propanol. 1H-NMR (600 MHz, DMSO-d6): δ 7.75 (d, J=8.10 Hz, 1H, Ar—H), 7.63 (t, J=7.62 Hz, 1H, Ar—H), 7.58 (d, J=7.80 Hz, 1H, Ar—H), 7.42 (t, J=7.50, 1H, Ar—H), 4.73 (t, J=5.30 Hz, 1H, OH), 3.50 (m, 2H, CH2), 3.19 (m, 1H, CH), 1.21 (d, J=6.90 Hz, 3H, CH3). TLC: 20% ethyl acetate in hexane, Rf=0.3.

1. washThe solution was washed with a molar solution of HCl (25 mL)
2. extractionextracted with ethyl acetate (3×100 mL)
3. dry with materialThe organic portion was dried (MgSO4)
4. filtrationfiltered
5. customthe solvent was removed in vacuo
6. customThe crude product was purified on a silica gel column
7. washElution of the column with 20-30% ethyl acetate in hexanes

ORD-Eintrag

ord-9d6c2a5cc9fe4106bebef73636da7bca

Quelldatensatz

uspto-grants-2005_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06965040B1