1,4-Dihydronaphthalene → 2,3-Epoxy-1,2,3,4-tetrahydronaphthalene

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Reaction Steps

A solution of 1,4-dihydronaphthalene (32.5 g, 0.25 M) in 300 ml chloroform is cooled in an ice bath and, while stirring, is treated portionwise with 61 g (~20% excess) of 85% m-chloroperbenzoic acid. The mixture is stirred overnight at room temperature. After cooling in an ice bath, the solids are removed by filtration. The filtrate is washed twice with 5% K2CO3 solution, dried over MgSO4, filtered and the solvent is removed in vacuo leaving 37.7 g of yellow partially crystalline material. This is distilled from a small amount of solid K2CO3. After removal of some low boiling material, 16.0 g (44%) of the desired epoxide is collected, boiling point 95°-110° at 0.1 mm.

Provenance & Evidence