Acetic Acid → (R)-2-(4-(Benzyloxy)-3-nitrophenyl)oxirane

Participants

Reaction Steps

151.8 g (0.49 mol) of 1-(4-benzyloxy-3-nitrophenyl)-2-chloroethanol was dissolved in THF (0.75 L) and treated dropwise with NaOH (4 mol/L, 182 mL, 0.73 mol). After 1 hour, AcOH (30 mL) was added followed by water (2.5 L). The mixture was cooled and the precipitated product was recovered by filtration and dried under vacuum at 65° C. Yield: 133.0 g (99.3%); mass spectroscopy: [M+H]+=272; m.p.=66° C.; e.e. 99.5%.

Provenance & Evidence