Reaktion #214664

Reaktionsgleichung

dichloroacetyl chloride

benzene

cyclohexanone

ethanolamine

→

product

N-dichloroacetyl-1-oxa-4-azaspiro[4,5]decane

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONFrom a boiling mixture of 64 g
2. 2
   workup.DISTILLATIONis continuously distilled off
3. 3
   Sonstigeof water are separated
4. 4
   TemperaturThe reaction mixture is then cooled
5. 5
   workup.ADDITION(0.55 moles) of a 40% aqueous sodium hydroxide solution are added
6. 6
   workup.ADDITIONfollowed by dropwise addition of 74 g
7. 7
   Waschenwashed with an aqueous hydrochloric acid solution and subsequently with water
8. 8
   SonstigeFrom the neutral mixture obtained benzene
9. 9
   workup.DISTILLATIONis distilled off in vacuo
10. 10
    Sonstige(0.4 moles) of a greenish-white crystalline substance are obtained
11. 11
    SonstigeRecrystallization from absolute ethanol

Vorschrift

From a boiling mixture of 64 g. (0.645 moles) of cyclohexanone and 30 g. (0.491 moles) of ethanolamine in 100 ml. of benzene the water formed is continuously distilled off. Boiling is continued until 8.8 ml. of water are separated. The reaction mixture is then cooled, 55 g. (0.55 moles) of a 40% aqueous sodium hydroxide solution are added followed by dropwise addition of 74 g. (0.5 moles) of dichloroacetyl chloride with external salt/ice cooling. The mixture is stirred for two additional hours at room temperature and thereafter washed with an aqueous hydrochloric acid solution and subsequently with water. From the neutral mixture obtained benzene is distilled off in vacuo. 10 g. (0.4 moles) of a greenish-white crystalline substance are obtained. Recrystallization from absolute ethanol affords a white crystalline product melting at 105.5° to 107° C. The structure of the named compound can be verified by IR spectrum analysis.

Quelle