Reacción #74776

Ecuación de reacción

1,4-dihydronaphthalene

m-chloroperbenzoic acid

→

1a,2,7,7a-Tetrahydronaphth[2,3-b]oxirane

Disolventes

chloroform

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGThe mixture is stirred overnight at room temperature
2. 2
   TemperaturaAfter cooling in an ice bath
3. 3
   Otrothe solids are removed by filtration
4. 4
   LavadoThe filtrate is washed twice with 5% K2CO3 solution
5. 5
   Secadodried over MgSO4
6. 6
   Filtraciónfiltered
7. 7
   Otrothe solvent is removed in vacuo
8. 8
   Otroleaving 37.7 g of yellow partially crystalline material
9. 9
   workup.DISTILLATIONThis is distilled from a small amount of solid K2CO3
10. 10
    OtroAfter removal of some low boiling material, 16.0 g (44%) of the desired epoxide
11. 11
    Otrois collected

Procedimiento

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.

Fuente