Reaction #502087

Reaction equation

1,3-Dioxalane

Et2O

acetyl chloride

Et2O

→

product

Acetoxyethyloxymethylchloride

Conditions

Workup

1. 1
   OtherA 5 L three-neck flask was fitted with mechanical stirrer
2. 2
   Otherthermometer, 500 mL additional funnel and argon purged
3. 3
   OtherA cold water bath was used
4. 4
   Temperaturewithout external cooling for 4 h
5. 5
   Otherreaction self
6. 6
   Temperatureheating at 20-25° C. for about 1 h
7. 7
   workup.WAITStood for 3 days
8. 8
   Otherformed an orange solution
9. 9
   workup.DISTILLATIONStrip Et2O on rotavap (water aspirator) until no more distilled at 35° C. bath

Procedure

A 5 L three-neck flask was fitted with mechanical stirrer, thermometer, 500 mL additional funnel and argon purged. 1,3-Dioxalane (140 mL, 2.00 mol) in anhydrous Et2O (800 mL) and 1.0 M ZnCl2/Et2O (7.5 mL, 0.007 mol) were added. A solution of acetyl chloride (157 mL, 2.20 mol) in Et2O (200 mL) was added dropwise through an additional funnel over 20 min. A cold water bath was used to maintain temperature between 19-27° C. throughout. Continue stirring without external cooling for 4 h, reaction self heating at 20-25° C. for about 1 h. A clear, colorless solution retained under argon overnight. Stood for 3 days and formed an orange solution. Strip Et2O on rotavap (water aspirator) until no more distilled at 35° C. bath. A quantitative yield of product 318 g (theoretical yield 306 g) was obtained.

Source