Reaction #880

Reaction equation

potassium tert-butoxide

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

→

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

Yield 77.6%

Solvents

ether

ether

Conditions

Workup

1. 1
   Otherreacted at room temperature for 3 hrs
2. 2
   workup.ADDITIONwas slowly added to the reaction mixture
3. 3
   Othersubjected to reaction at room temperature for 4 hrs
4. 4
   OtherAfter completion of the reaction
5. 5
   Filtrationthe produced solid by-product was filtered off
6. 6
   Washwashed with distilled water and saturated saline
7. 7
   WashThe organic phase washed
8. 8
   Dryingwas dried over anhydrous magnesium sulfate
9. 9
   Otherthe solvent was removed by distillation under reduced pressure
10. 10
    OtherThe reaction mixture was purified by Silica gel column chromatography

Procedure

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. 25.6 g of the above 4-(2-[1,3]-dioxane-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 19.7 g of 2-[2-(4-vinylphenoxy)ethyl]-[1,3]-dioxane, represented by the following formula: ##STR9##

Source