Réaction #55930

Équation de réaction

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

carbonate

water

→

3,7-dimethyl-4-[(1-ethoxyethoxy)]-6-octen-1-ol

Solvants

methanol

Conditions de réaction

Traitement

1. 1
   AutreMost of the methanol is removed in vacuo
2. 2
   workup.ADDITIONthe residue is treated with ethyl acetate (500 ml) and water (200 ml)
3. 3
   SéchageThe organic phase is dried (Na2SO4)
4. 4
   Autreevaporated in vacuo
5. 5
   Autreto give the crude product
6. 6
   AutreThis material is further purified by column chromatography on silica gel (25 g, 15% ethyl acetate in hexane)

Mode opératoire

A mixture of 8-acetoxy-2,6-dimethyl-5-[(1-ethoxyethoxy)]-2-octene (0.5 mmole), saturated potassim carbonate solution (9 ml), water (6 ml) and methanol (100 ml) is stirred for 3 hours at room temperature. Most of the methanol is removed in vacuo and the residue is treated with ethyl acetate (500 ml) and water (200 ml). The organic phase is dried (Na2SO4) and evaporated in vacuo to give the crude product. This material is further purified by column chromatography on silica gel (25 g, 15% ethyl acetate in hexane) to give 3,7-dimethyl-4-[(1-ethoxyethoxy)]-6-octen-1-ol as a colorless oil.

Source