Reaktion #2006437

Reaktionsgleichung

cyclooctanone

ethyl magnesium bromide

sodium bicarbonate

→

alcohol

Ausbeute 32.0%

1-Ethylcyclooctanol

Ausbeute 32.0%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeTo a 1000-mL 3-necked round bottom flask equipped with a 500-mL pressure
2. 2
   workup.ADDITIONaddition funnel, a nitrogen inlet with thermocouple and an overhead stirrer
3. 3
   workup.WAITfollowed by 8 hours
4. 4
   Temperaturat reflux
5. 5
   FiltrationThe resulting suspension was filtered through a bed of Celite
6. 6
   workup.ADDITIONthe filtrate diluted with 500 mL of ether
7. 7
   Trocknenthe combined organics washed several times with saturated sodium bicarbonate, once with brine and then dried for 1 hr over anhydrous magnesium sulfate
8. 8
   FiltrationFiltration and removal of the solvent at reduced pressure
9. 9
   Sonstigeresulted in a light-colored oil which
10. 10
    workup.DISTILLATIONwas distilled twice from Na2CO3 through a base-washed 15 cm Vigreux (bp 65° C.@ 1 mmHg)

Vorschrift

To a 1000-mL 3-necked round bottom flask equipped with a 500-mL pressure equalizing addition funnel, a nitrogen inlet with thermocouple and an overhead stirrer was added 100 g (0.79 mol) of cyclooctanone dissolved in 250 mL of dry tetrahydrofuran. The addition funnel was charged with 290 mL (0.869 mol, 10% excess) of ethyl magnesium bromide (2.0M solution in ether) which was then added to the cooled ketone over 2 hours. Stirring was continued at room temperature overnight followed by 8 hours at reflux. Excess Grignard reagent was discharged by the cautious addition of 100 mL of saturated sodium bicarbonate solution. The resulting suspension was filtered through a bed of Celite, the filtrate diluted with 500 mL of ether and the combined organics washed several times with saturated sodium bicarbonate, once with brine and then dried for 1 hr over anhydrous magnesium sulfate. Filtration and removal of the solvent at reduced pressure resulted in a light-colored oil which was distilled twice from Na2CO3 through a base-washed 15 cm Vigreux (bp 65° C.@ 1 mmHg) to yield 39 g (32%) of the title alcohol as a clear, colorless oil.

Quelle