Ethanol → 2-(6-Carbethoxyoctyl)-2-cyclopentenone
Reaction equation
[C:1]([CH:4]([CH2:16][CH3:17])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[C:11](=[O:15])[CH2:12][CH2:13][CH:14]=1)([OH:3])=[O:2].S(Cl)(Cl)=O.[CH2:22](O)[CH3:23]>>[C:1]([CH:4]([CH2:16][CH3:17])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[C:11](=[O:15])[CH2:12][CH2:13][CH:14]=1)([O:3][CH2:22][CH3:23])=[O:2]Participants
4
Procedure
Treatment of 2-(6-carboxyoctyl)-2-cyclopentenone (Example 154) with thionyl chloride and then treatment of the acid chloride with ethanol in the manner described in Example 264 give an amber oil. The oil is placed on a magnesia-silica gel column and eluted with 3:1 benzene:ether. The solvent is removed and the residue is distilled, b.p. 122° C. (0.06 mm).
Workup
- customgive an amber oil
- washeluted with 3:1 benzene