[Synthesis]
1. Sodium borohydride (NaBH4, 2.20 g, 58.1 mmol) was slowly added to a solution of methanol (MeOH, 100 mL) containing 1-(3-nitrophenyl)ethanone (ID29, 2.32 g, 14.0 mmol) at 0°C.
2. The reaction mixture was stirred continuously at 0 °C for 1 hour.
3. After completion of the reaction, most of the methanol was removed by concentration under reduced pressure. 4.
4. The residue was diluted with ethyl acetate (EtOAc, 150 mL) and water (50 mL) and the organic layer was separated.
5. The organic layer was washed sequentially with water (50 mL) and saturated saline (50 mL) and then dried over anhydrous sodium sulfate (Na2SO4).
6. The desiccant was removed by filtration, and the filtrate was concentrated under reduced pressure to obtain the crude product.
7. The crude product was dried under vacuum to afford 1-(3-nitrophenyl)ethanol (ID30) as a pale yellow oil (2.23 g, 95% yield). 8. The structure of the product was determined by 1H NMR.
8. The structure of the product was confirmed by 1H NMR (CDCl3, 600 MHz): δ 8.25 (s, 1H), 8.12 (ddd, J = 8.4, 1.2, 1.2 Hz, 1H), 7.72 (d, J = 7.2 Hz, 1H), 7.52 (dd, J = 8.1, 8.1 Hz, 1H), 5.02 (q, J = 6.6 Hz, 1H), 2.07 (s, J = 6.6 Hz, 1H), 5.02 (q, J = 6.6 Hz, 1H), 5.02 (q, J = 6.6 Hz, 1H), 2.02 (q, J = 6.6 Hz, 1H), 2.07 (s), 2.07 (s), 1H). ), 2.07 (s, 1H), 1.54 (d, J = 6.6 Hz, 3H). |
[References]
[1] Green Chemistry, 2018, vol. 20, # 9, p. 2118 - 2124
[2] Journal of the Iranian Chemical Society, 2015, vol. 12, # 7, p. 1221 - 1226
[3] Synthetic Communications, 1990, vol. 20, # 6, p. 849 - 854
[4] Chemistry Letters, 1987, p. 181 - 184
[5] Synthesis, 2009, # 23, p. 4058 - 4062 |