Example 26: Synthesis of 2-(2-nitrophenyl)ethanol (8a)
To a stirred solution of ethyl (E)-3-(2-nitrophenyl)acrylate (9) (7.0 g, 31.7 mmol) in 95% ethanol (100 mL) was added CO2Cl2-6H2O (377 mg, 5 mol%) and diisopropylamine (320 mg, 10 mol%) at 25 °C, followed by the slow addition of NaBH4 (4.8 g 126.8 mmol). The reaction mixture was stirred at 50 °C for 24 hours. Upon completion of the reaction (monitored by TLC), the reaction was quenched by the addition of water (20 mL) and ethyl acetate (100 mL). The organic layer was separated and the aqueous layer was extracted with ethyl acetate (2 x 50 mL). The combined organic layers were washed with brine (2 × 20 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography using petroleum ether/ethyl acetate (7:3 v/v) as eluent to give alcohol 8a (5.74 g) as a gel.
Yield: 85%;
IR (CHCl3): νmax 857, 968, 1029, 1060, 1245, 1440, 1507, 3430 cm-1;
1H NMR (200 MHz, CDCl3): δ 1.85-1.99 (m, 2H), 2.14 (br s, 1H), 2.98 (t, J = 7.6 Hz, 2H), 3.70 (t, J = 6.2 Hz, 2H), 7.31-7.55 (m, 3H), 7.86 (d, J = 7.7 Hz, 1H);
13C NMR (50 MHz, CDCl3): δ 29.1, 33.2, 61.6, 64.4, 126.8, 131.8, 132.8, 136.7, 149.1;
Elemental analysis (C9H11NO3) calculated values: C, 59.66; H, 6.12; N, 7.73; measured values: C, 59.71; H, 6.15; N, 7.79%.
