Reaktion #1241240

Reaktionsgleichung

p-ethylanisole

ether

ammonia

ammonia

lithium

→

4-Ethyl-3-cyclohexen-1-one

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturTo a stirred refluxing
2. 2
   workup.ADDITIONthere was added portionwise, at -35 ° to -32° C.
3. 3
   workup.WAITAfter an additional 15 minutes
4. 4
   Sonstigeto evaporate
5. 5
   workup.WAITon standing overnight
6. 6
   workup.ADDITIONThe residue was poured into 1 l of ice water
7. 7
   Extraktionextracted twice with ether
8. 8
   EinengenThe combined ether extracts concentrated to a volume of about 300 ml
9. 9
   workup.STIRRINGwas stirred with 250 ml of water containing 46 g of oxalic acid overnight at ambient temperature
10. 10
    workup.ADDITIONThis mixture was diluted with 1 liter of water
11. 11
    Extraktionextracted twice with ether
12. 12
    WaschenThe combined ether extracts were washed with 5% sodium bicarbonate
13. 13
    SonstigeAfter drying
14. 14
    Einengenthe ether solution was vacuum-concentrated to a residue of 104.4 g of desired product
15. 15
    workup.DISTILLATIONused without distillation

Vorschrift

To a stirred refluxing mixture of 600 ml of dry ether and 1600 ml of liquid ammonia was added 136 g of p-ethylanisole. After 15 minutes, there was added portionwise, at -35 ° to -32° C., a 26.4 g quantity of lithium ribbon over 0.5-1 hour. After an additional 15 minutes, 193 g of dry ethanol was added dropwise at -35° to -32° C. Stirring was continued until the blue color disappeared, and the ammonia was allowed to evaporate on standing overnight. The residue was poured into 1 l of ice water and extracted twice with ether. The combined ether extracts concentrated to a volume of about 300 ml was stirred with 250 ml of water containing 46 g of oxalic acid overnight at ambient temperature. This mixture was diluted with 1 liter of water and extracted twice with ether. The combined ether extracts were washed with 5% sodium bicarbonate and then with water. After drying, the ether solution was vacuum-concentrated to a residue of 104.4 g of desired product; it was 94% pure by GLC analysis and used without distillation.

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