3-Nitrostyrene → 2-(3-Nitrophenyl)oxirane

Participants

Reaction Steps

A solution of 3-nitrostyrene (1.0 g, 6.70 mmol) in CH2Cl2 (10 mL) was cooled in an ice bath. 3-Chloroperoxybenzoic acid (57% pure) (2.23 g, 7.38 mmol) was added in one batch and the stirring was continued for 18 h. The reaction mixture was concentrated to a residue and diluted with CCl4 (20 mL). Precipitated m-chlorobenzoic acid was removed by filtration and the flitrate was washed with a 50:50 mixture of 5% aq. NaHCO3 and 5% aq. NaHSO3 (100 mL). The organic extract was dried over Na2SO4 and concentrated under reduced pressure to yield 0.70 g (64%) of a yellow oil. 1H NMR (CDCl3) δ2.81 (m, 1, CH), 3.20 (m, 1, CH--), 3.97 (m, 1, --CH--), 7.62 (m, 2, phenyl), 8.16 (m, 2, phenyl).

Provenance & Evidence