m-Chloroperbenzoic acid → 2-((1-Nitrocyclohexyl)methyl)oxirane

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Reaction Steps

A 1 neck 500 mL round bottom flask equipped with dropping funnel, temperature controller, nitrogen outlet, stir bar and condenser is charged with approximately 37 g of mCPBA (72% pure, 0.15 mols) and 100 mL of CH2Cl2. The reaction slurry is warmed to dissolve all the solids in CH2Cl2. Once a clear solution is obtained, 20 g (0.12 mols) of 1-allyl-1-nitrocyclohexane (11) is added slowly. After complete addition, the reaction is refluxed for 2 hrs and stirred for 48 h at room temperature. The progress of the reaction is monitored by GC. After the duration of almost 50 h, the composition of the epoxide in the reaction mixture is approximately 38.5%. Solid mCPBA that crashes out of solution is removed by gravity filtration. The organic layer is washed with 10% Na2CO3 (3×30 mL) followed by brine (3×30 mL). The organic layer is dried under MgSO4 and excess solvent stripped off under rotary evaporator. This affords 11.8 g of crude material. The retention time of the epoxide on the GC is 18.3 minutes. The presence of epoxide is confirmed by GC-MS CI. The parent ion is not detected due to the labile nature of NO2 groups. However, the fragment minus the NO2 is observed. CI GC/MS, [C9H15O]+=139.

Provenance & Evidence