Acetic Acid → 1-Nitro-2-phenylethane

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). β-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 CH2Cl12. The organic phase was washed with water (2×30 mL) and brine (1×30 mL), dried (Na2SO4), filtered and evaporated in vacuo obtaining 4 (8.4.0 g, 83%) as yellow oil. ESI-MS: 152 (MH+) (Calc. for C8H9NO2: 151).

1. customIn a 500 mL two-necked flask equipped with a thermometer
2. customthe temperature below 30° C
3. customA fine slurry formed during the addition
4. additionAfter the addition the reaction mixture
5. concentrationthe clear solution was then concentrated in vacuo
6. dissolutionthe residue was dissolved in water
7. extractionextracted twice with CH2Cl12
8. washThe organic phase was washed with water (2×30 mL) and brine (1×30 mL)
9. dry with materialdried (Na2SO4)
10. filtrationfiltered
11. customevaporated in vacuo
12. customobtaining 4 (8.4.0 g, 83%) as yellow oil

ORD record

ord-dfe16dfcd0e844a2a2fc50556fc14a84

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07893223B2