Reaktion #510130

Reaktionsgleichung

sodium hydroxide

cyclohexanone

1,3-propanediol

triethyl orthoformate

→

cyclohexanone trimethylene ketal

Ausbeute 55.3%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe resulting mixture was stirred at room temperature under a nitrogen atmosphere for 1 hour
2. 2
   workup.STIRRINGAfter stirring
3. 3
   workup.ADDITIONwas added to the reaction mixture
4. 4
   workup.STIRRINGwith stirring
5. 5
   Extraktionthe resulting mixture was extracted with dichloromethane
6. 6
   WaschenThe extract was washed with water
7. 7
   Trocknendried over anhydrous sodium sulfate
8. 8
   FiltrationAfter filtration
9. 9
   Sonstigethe solvent was removed in vacuo
10. 10
    workup.DISTILLATIONthe residue was purified by reduced-pressure distillation

Vorschrift

To a solution of cyclohexanone (32 ml, 0.31 mol) in dry dichloromethane (950 ml) were added successively 1,3-propanediol (33.5 ml, 0.46 mol), triethyl orthoformate (51.5 ml, 0.31 mol) and zirconium chloride (1.44 g, 6.18 mmol) with stirring, and the resulting mixture was stirred at room temperature under a nitrogen atmosphere for 1 hour. After stirring, ice-chilled 1N aqueous sodium hydroxide solution (1.5 l) was added to the reaction mixture with stirring, and the resulting mixture was extracted with dichloromethane. The extract was washed with water and dried over anhydrous sodium sulfate. After filtration, the solvent was removed in vacuo, and the residue was purified by reduced-pressure distillation to afford cyclohexanone trimethylene ketal (26.8 g, yield: 55%).

Quelle