Réaction #55929

Équation de réaction

sodium bicarbonate

8-acetoxy-2,6-dimethyl-5-hydroxy-2-octene

ethyl vinylether

p-toluenesulfonic acid monohydrate

→

8-acetoxy-2,6-dimethyl-5-[(1-ethoxyethoxy)]-2-octene

Solvants

ether

ether

Conditions de réaction

Traitement

1. 1
   SéchageThe organic phase is dried (Na2SO4)
2. 2
   Autreevaporated in vacuo
3. 3
   Autreto give the crude product
4. 4
   AutreThe crude material is further purified by column chromatography on silica gel (25 g, 5% ethyl acetate in hexane)

Mode opératoire

A mixture of 8-acetoxy-2,6-dimethyl-5-hydroxy-2-octene (2.27 g, 10.6 mmole), ethyl vinylether (0.82 g. 11.4 mmole), p-toluenesulfonic acid monohydrate (catalytic amount) and ether (50 ml) is stirred at room temperature for 16 hours. The resulting mixture is treated with ether (150 ml) and washes with 5% sodium bicarbonate solution (2×100 ml). The organic phase is dried (Na2SO4), and evaporated in vacuo to give the crude product. The crude material is further purified by column chromatography on silica gel (25 g, 5% ethyl acetate in hexane) to give 8-acetoxy-2,6-dimethyl-5-[(1-ethoxyethoxy)]-2-octene as a colorless oil.

Source