Reacción #438674

Ecuación de reacción

(1,3-dioxolan-4-yl)methyl 5-norbornene-2-carboxylate

glycerol formal

triethylamine

5-norbornene-2-carbonyl chloride

→

1,3-dioxan-5-yl 5-norbornene-2-carboxylate

Rendimiento 95.0%

Disolventes

toluene

water

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added over one hour at 20° C
2. 2
   Otrothe reaction
3. 3
   Otroto separate
4. 4
   LavadoThe organic layer was washed with water and saturated sodium chloride water
5. 5
   Secadodried over anhydrous sodium sulfate
6. 6
   Concentraciónconcentrated in vacuum
7. 7
   workup.DISTILLATIONIt was further purified by vacuum distillation

Procedimiento

To a mixture of 104 g of glycerol formal, 111 g of triethylamine and 300 ml of toluene, 157 g of 5-norbornene-2-carbonyl chloride was added over one hour at 20° C. After 5 hours of stirring, 200 ml of water was added to stop the reaction and the mixture was allowed to separate. The organic layer was washed with water and saturated sodium chloride water, dried over anhydrous sodium sulfate, and concentrated in vacuum. It was further purified by vacuum distillation, obtaining 213 g of a mixture of (1,3-dioxolan-4-yl)methyl 5-norbornene-2-carboxylate and 1,3-dioxan-5-yl 5-norbornene-2-carboxylate (boiling point 111-115° C./530 Pa, yield 95%).

Fuente