Reaktion #552638

Reaktionsgleichung

1,10-dibromodecane

4-hydroxyphenyl propan-2-one

sodium

→

10-(4-acetonylphenoxy)decyl bromide

Lösungsmittel

methanol

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturunder reflux
2. 2
   Temperaturthe reaction mixture heated for 3 h
3. 3
   Temperaturto cool
4. 4
   Sonstigethe solvent was removed in vacuo
5. 5
   SonstigeThe residue was partitioned between diethylether and water
6. 6
   Sonstigethe organic layer separated
7. 7
   Trocknendried (magnesium sulphate)
8. 8
   Sonstigethe solvent removed in vacuo
9. 9
   Sonstigeto give an oil which
10. 10
    Sonstigewas chromatographed on silica
11. 11
    WaschenElution with chloroform

Vorschrift

A solution of 4-hydroxyphenyl propan-2-one, ethylene ketal (5.26 g) in methanol at room temperature, was treated with sodium (0.66 g) and allowed to stir for 10 minutes. The resulting solution was then added dropwise over 15 minutes to a solution of 1,10-dibromodecane (9.0 g) in methanol under reflux and the reaction mixture heated for 3 h. The mixture was allowed to cool and the solvent was removed in vacuo. The residue was partitioned between diethylether and water, the organic layer separated, dried (magnesium sulphate), and the solvent removed in vacuo to give an oil which was chromatographed on silica. Elution with chloroform gave 10-(4-acetonylphenoxy)decyl bromide, ethylene ketal (3.0 g) as an oil.

Quelle