Реакция #55930

Уравнение реакции

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

carbonate

water

→

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

Растворители

methanol

Условия реакции

Обработка

1. 1
   ДругоеMost 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
   СушкаThe organic phase is dried (Na2SO4)
4. 4
   Другоеevaporated in vacuo
5. 5
   Другоеto give the crude product
6. 6
   ДругоеThis material is further purified by column chromatography on silica gel (25 g, 15% ethyl acetate in hexane)

Методика

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.

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