Reaction #55930

Reaction equation

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

carbonate

water

→

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

Solvents

methanol

Conditions

Workup

1. 1
   OtherMost 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
   DryingThe organic phase is dried (Na2SO4)
4. 4
   Otherevaporated in vacuo
5. 5
   Otherto give the crude product
6. 6
   OtherThis material is further purified by column chromatography on silica gel (25 g, 15% ethyl acetate in hexane)

Procedure

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