Reacción #882

Ecuación de reacción

potassium tert-butoxide

4-(2-[1,3]-dioxolan-2-yl-ethoxy)benzaldehyde

→

2-[2-(4-vinylphenoxy)ethyl]-[1,3]-dioxolan

Rendimiento 88.5%

Disolventes

ether

ether

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroreacted at room temperature for 3 hrs
2. 2
   workup.ADDITIONwas slowly added to the reaction mixture
3. 3
   Otrosubjected to reaction at room temperature for 4 hrs
4. 4
   OtroAfter completion of the reaction
5. 5
   Filtraciónthe produced solid by-product was filtered off
6. 6
   Lavadowashed with distilled water and saturated saline
7. 7
   LavadoThe organic phase washed
8. 8
   Secadowas dried over anhydrous magnesium sulfate
9. 9
   Otrothe solvent was removed by distillation under reduced pressure
10. 10
    OtroThe reaction mixture was purified by Silica gel column chromatography

Procedimiento

In another 2 liter flask, 57.2 g of methyl triphenylphosphonium bromide was placed. 500 ml of anhydrous ether was poured and then, stirred. To the resulting solution was slowly added 18.0 g of potassium tert-butoxide and reacted at room temperature for 3 hrs. 23.7 g of the above 4-(2-[1,3]-dioxolan-2-yl-ethoxy)benzaldehyde was dissolved in 200 ml of anhydrous ether and was slowly added to the reaction mixture and then subjected to reaction at room temperature for 4 hrs. After completion of the reaction, the produced solid by-product was filtered off and washed with distilled water and saturated saline. The organic phase washed was dried over anhydrous magnesium sulfate and the solvent was removed by distillation under reduced pressure. The reaction mixture was purified by Silica gel column chromatography to obtain 20.8 g of 2-[2-(4-vinylphenoxy)ethyl]-[1,3]-dioxolan, represented by the following formula: ##STR10##

Fuente