Reacción #310969

Ecuación de reacción

HCl

HCl

5-methyl-2-furylallylcarbinol

NaOH

sodium chloride

NaOH

→

2-allyl-3-hydroxy-3-methyl-4-cyclopentenone

Disolventes

water

ethyl acetate n-hexane

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrowas elevated up to 100° C.
2. 2
   Temperaturato reflux
3. 3
   Temperaturaunder reflux for 7 hours
4. 4
   Temperaturawhile maintaining a pH value of 5 to 5.5
5. 5
   Extracciónthe mixture was extracted with toluene (70 ml) five times
6. 6
   OtroFrom the extract, toluene was removed by distillation at 60° C. under reduced pressure
7. 7
   Otroto give an oily substance (10.1 g), which

Procedimiento

In a reaction vessel, water (150 ml) and tri-n-octylmethylammonium chloride (450 mg) were charged, and the pH value was adjusted to 5.5 with an aqueous 1/3 N HCl solution and an aqueous 1/3 N NaOH solution. Then, 5-methyl-2-furylallylcarbinol (11.0 g) was added thereto, and the temperature was elevated up to 100° C. to reflux. The mixture was stirred under reflux for 7 hours while maintaining a pH value of 5 to 5.5 by the addition of an aqueous 1/3 N NaOH solution and an aqueous 1/3 N HCl solution. After cooling to 40° C., sodium chloride (30 g) was added, and the mixture was extracted with toluene (70 ml) five times. From the extract, toluene was removed by distillation at 60° C. under reduced pressure to give an oily substance (10.1 g), which was subjected to chromatography on silica gel (100 g) with a mixture of ethyl acetate-n-hexane (1:2 by volume) as the developing solvent to obtain 2-allyl-3-hydroxy-3-methyl-4-cyclopentenone (7.1 g). Yield, 64.5%.

Fuente