Reacción #1697870

Ecuación de reacción

4-bromo-1-methyl-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-5-ol

p-toluenesulfonic acid monohydrate

→

1-bromo-4-methyl-6,7-dihydro-5H-benzo[a]cycloheptene

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaunder reflux in a reaction vessel
2. 2
   Otroequipped with a Dean-Stark trap under dehydrating conditions for 0.5 hr
3. 3
   Otrothe solvent was evaporated under reduced pressure
4. 4
   OtroThe obtained crude product
5. 5
   Otrowas purified by silica gel column chromatography (hexane)
6. 6
   Otroto give the objective substance

Procedimiento

A solution of 4-bromo-1-methyl-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-5-ol (6.213 g, 24.35 mmol) and p-toluenesulfonic acid monohydrate (0.46 g, 2.44 mmol) in toluene (100 ml) was heated under reflux in a reaction vessel equipped with a Dean-Stark trap under dehydrating conditions for 0.5 hr. After the reaction solution was cooled to room temperature, the solvent was evaporated under reduced pressure. The obtained crude product was purified by silica gel column chromatography (hexane) to give the objective substance.

Fuente