Reacción #65219

Ecuación de reacción

ethanol

5-(3,5-di-tert-butyl-4-hydroxybenzoyl)-6-methoxyindan

boron tribromide dichloromethane

→

5-(3,5-di -tert-butyl-4-hydroxybenzoyl)-6-hydroxyindan

Rendimiento 83.6%

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooling
2. 2
   workup.STIRRINGThe mixture was stirred under ice-
3. 3
   Temperaturacooling for 15 minutes
4. 4
   LavadoThe mixture was then washed with water
5. 5
   Secadodried (MgSO4)
6. 6
   workup.DISTILLATIONthe solvent was distilled off
7. 7
   workup.ADDITIONTo the residue was added hexane

Procedimiento

To a solution of 5-(3,5-di-tert-butyl-4-hydroxybenzoyl)-6-methoxyindan (3.8 g) in dichloromethane (30 ml) was added boron tribromide-dichloromethane (1:2, 3 ml) dropwise with ice-cooling and stirring. The mixture was stirred under ice-cooling for 15 minutes, after which ethanol (5 ml) was added dropwise. The mixture was then washed with water and dried (MgSO4) and the solvent was distilled off. To the residue was added hexane to give crystals of 5-(3,5-di -tert-butyl-4-hydroxybenzoyl)-6-hydroxyindan (3.06 g, 83.6% ) . Recrystallization from ethanol gave light yellow prisms, m.p. 155°-156° C.

Fuente