Acetic Acid → 1-Nitro-2-phenylethane
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[BH4-].[Na+].[N+:3]([CH:6]=[CH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([O-:5])=[O:4].C(O)(=O)C>O1CCOCC1.C(O)C.O1CCOCC1>[N+:3]([CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([O-:5])=[O:4][BH4-].[Na+].[N+:3]([CH:6]=[CH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([O-:5])=[O:4].C(O)(=O)C>O1CCOCC1.C(O)C.O1CCOCC1>[N+:3]([CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([O-:5])=[O:4]In a 500 mL two-necked flask equipped with a thermometer and a pressure-equalizing dropping funnel, NaBH4 (5.33 g, 0.140 mol) was suspended in 1,4-dioxane/ethanol (100 mL/30 ml). ≈-Nitrostyrene (3, 10.0 g, 67.0 mmol) in 1,4-dioxane (100 mL) was added dropwise to the solution over 45 minutes, keeping the temperature below 30° C. A fine slurry formed during the addition. After the addition the reaction mixture was stirred overnight, then ice/water (125 mL) was added, and a 50% solution of acetic acid was added to neutralize excess NaBH4; the clear solution was then concentrated in vacuo and the residue was dissolved in water and extracted twice with CH2Cl2. The organic phase was washed with water (2×30 mL) and brine (1×30 mL), dried (Na2SO4), filtered and evaporated in vacuo obtaining 4 (8.40 g, 83%) as yellow oil. ESI-MS: 152 (MH+) (Calc. for C8H9NO2: 151).
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