Reaktion #478677

Reaktionsgleichung

water

Aluminum chloride

glutaryl chloride

benzene

→

1,5-diphenyl-1,5-pentanedione

Ausbeute 27.0%

Lösungsmittel

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONis introduced into a 100 mL two-necked round-bottomed flask under an inert atmosphere
2. 2
   workup.ADDITIONis added dropwise at room temperature
3. 3
   TemperaturThe mixture is then refluxed for 24 hours
4. 4
   workup.ADDITIONpoured into a crystallizing basin
5. 5
   workup.ADDITIONcontaining 20 mL of 10%
6. 6
   FiltrationA black solid forms, and is filtered off on a Büchner funnel
7. 7
   ExtraktionThe yellow organic phase is then extracted with ethyl acetate
8. 8
   Trocknendried over MgSO4
9. 9
   Filtrationfiltered
10. 10
    Einengenconcentrated on a rotary evaporator
11. 11
    Sonstigerecrystallized from 20 mL of methanol
12. 12
    SonstigeThe product obtained
13. 13
    SonstigeThe reaction yield is 27%

Vorschrift

A solution of glutaryl chloride (10 mmol, 1.3 mL) dissolved in anhydrous dichloromethane (20 mL) is introduced into a 100 mL two-necked round-bottomed flask under an inert atmosphere. Aluminum chloride (30 mmol, 4.00 g) is added to the mixture, which immediately turns orange-yellow. A solution of benzene (20 mmol, 1.8 mL) dissolved in anhydrous dichloromethane (10 mL) is added dropwise at room temperature. The solution becomes bright red. The mixture is then refluxed for 24 hours, and turns brown-black. The mixture is then cooled to room temperature and poured into a crystallizing basin containing 20 mL of 10% acidified water, with stirring. A black solid forms, and is filtered off on a Büchner funnel. The yellow organic phase is then extracted with ethyl acetate, dried over MgSO4, filtered, concentrated on a rotary evaporator and recrystallized from 20 mL of methanol. The product obtained is a white solid in a mass of 680 mg. The reaction yield is 27%.

Quelle