m-Chloroperbenzoic acid → 4,4-Dimethyl-3,5,8-trioxabicyclo[5.1.0]octane

Participants

Reaction Steps

To a suspension of m-chloroperbenzoic acid (74% pure; 78.15 g; 0.33 mole) in methylene chloride (600 ml), was added a solution of 2,2-dimethyl-4,7-dihydro-1,3-dioxepin (II) (41.0 g, 0.32 mole) in methylene chloride (200 ml) during 30 min at room temperature. The mixture was refluxed for 8 hrs and then cooled in ice for 1 hr. The precipitated solid was filtered off and the organic filtrate was washed with 10% aqueous sodium sulfite (2×100 ml), saturated aqueous sodium bicarbonate (3×500 ml), 5% aqueous sodium hydroxide (2×250 ml) and brine (2×200 ml) and dried (MgSO4). Removal of the solvent followed by vacuum distillation of the residual oil gave the epoxide product (III) as a colorless liquid. 36.94 g (80% yield). b.p. 90°-92°/11 mm.

Provenance & Evidence