Reaction #881

Reaction equation

4-hydroxybenzaldehyde

2-(2-bromoethyl)-1,3-dioxane

potassium iodide

potassium carbonate

→

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

Yield 104.5%

Solvents

ethyl acetate

acetonitrile

Conditions

Workup

1. 1
   Otherreacted at 80° C. for 5 hr
2. 2
   Washwashed once with a saturated aqueous potassium carbonate solution
3. 3
   workup.DISTILLATIONdistilled water and saturated saline
4. 4
   DryingThe washed organic phase was dried over anhydrous magnesium sulfate
5. 5
   Otherthe solvent was removed

Procedure

In a 500 ml flask, 120 ml of acetonitrile, 13.8 g of 4-hydroxybenzaldehyde, 19.9 g of 2-(2-bromoethyl)-1,3-dioxane, 1.8 g of potassium iodide, and 35.8 g of potassium carbonate were placed and then, reacted at 80° C. for 5 hr. Thereafter, to the reaction mixture was added 200 ml of ethyl acetate and washed once with a saturated aqueous potassium carbonate solution, distilled water and saturated saline. The washed organic phase was dried over anhydrous magnesium sulfate and the solvent was removed, to give 23.7 g of 4-(2-[1,3]-dioxolan-2-yl-ethoxy)benzaldehyde.

Source