반응 #55584

반응 방정식

ethyl 9-oxodecanoate

ethylene glycol

p-toluenesulfonic acid

→

title compound

수율 83.5%

Ethyl 9-oxodecanoate ethylene ketal

수율 83.5%

용매

benzene

반응 조건

후처리

1. 1
   온도was refluxed for 4.5 hr with a Dean Stark trap
2. 2
   기타A 7.0 ml portion of water (theoretical=6.5 g) collected in the trap
3. 3
   세척was washed with saturated aqueous sodium bicarbonate
4. 4
   추출The aqueous phase was back-extracted twice with ether
5. 5
   건조The combined ether extracts were dried over Na2SO4
6. 6
   기타evaporated in vacuo
7. 7
   workup.DISTILLATIONdistilled in vacuo

실험 절차

A solution containing 77.5 g (362 mmol) of ethyl 9-oxodecanoate (prepared described in J. Amer. Chem. Soc., 68: 832 [1946]), 22.4 g (362 mmol) of ethylene glycol and 438 mg of p-toluenesulfonic acid in 150 ml of dry benzene was refluxed for 4.5 hr with a Dean Stark trap. A 7.0 ml portion of water (theoretical=6.5 g) collected in the trap. The solution was cooled to room temperature and then was washed with saturated aqueous sodium bicarbonate. The aqueous phase was back-extracted twice with ether. The combined ether extracts were dried over Na2SO4 and evaporated in vacuo and distilled in vacuo to give a 83.5% yield of the title compound. The product had the following physical characteristics:

출처