Reacción #1475992

Ecuación de reacción

water

potassium carbonate

thiophenol

(+)-(1R,2S,4R)-1,2-epoxy-8-p-menthene

→

thioether

Rendimiento 100.0%

(+)-(1S,2S,4R)-2-phenylthio-8-p-menthen-1-ol

Rendimiento 100.0%

Disolventes

toluene

dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas heated
2. 2
   Temperaturaunder reflux for 10 hours
3. 3
   Lavadothe separated organic layer was successively washed with water and with brine
4. 4
   Secadodried over sodium sulfate
5. 5
   Otroevaporated
6. 6
   workup.DISTILLATIONAfter distillation in a bulb apparatus

Procedimiento

A suspension of 164 g (1 M) of the above diastereomeric mixture, 83 g of potassium carbonate and 60.5 g (0.556 M) of thiophenol in a mixture of 380 ml of toluene and 20 ml of dimethylformamide was heated under reflux for 10 hours. After cooling to room temperature and addition of water, the separated organic layer was successively washed with water and with brine, dried over sodium sulfate and evaporated. After distillation in a bulb apparatus, the desired thioether (131 g; ca. 100% yield) was separated from unreacted (+)-(1R,2S,4R)-1,2-epoxy-8-p-menthene. The title compound thus prepared was characterized as follows:

Fuente