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ChemicalBook CAS DataBase List 1-(PHENYL) 2-NITROETHANE
6125-24-2

1-(PHENYL) 2-NITROETHANE synthesis

12synthesis methods
1-(Phenyl) 2-nitroethane is prepared:
1) from beta-Phenylethylamine by oxidation. The amine is obtained from Benzyl cyanide in liquid Ammonia with a Raney-Nickel catalyst, by hydrogenation.
2) by isolation from the essential oil of the leaves of Aniba canellila (in Brazil).
-

Yield: 75%

Reaction Conditions:

with hydrogenchloride;sodium tetrahydroborate;SiO2 in chloroform

Steps:

15.b 15b.
15b. 2-phenylnitroethane 2-Phenylnitroethene (5.12 g, 34.3 mmol, from step 15a) was dissolved in CHCl3 /i-PrOH (410:85 mL) and SiO2 (51.4 g) was added. NaBH4 (5.2 g, 137 mmol) was added in portions, and the mixture was stirred for 90 minutes at room temperature. HCl (0.5N, 100, mL) was added, and the mixture was stirred for 30 minutes. The layers were separated, and the aqueous phase was extracted with methylene chloride. The organic layers were combine, dried (MgSO4) and concentrated. The residue was chromatographed on silica gel (eluding with ether:hexanes 1:30) to give the title compound as an oil (3.89 g, 75%).

References:

Abbott Laboratories US5733912, 1998, A

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