Reaktion #55929

Reaktionsgleichung

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

Lösungsmittel

ether

ether

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle