Reaktion #468996

Reaktionsgleichung

4-chlorobiphenyl

succinic anhydride

aluminum chloride

→

4-(4′-chloro-biphenyl-4-yl)-4-oxo-butyric acid

Ausbeute 13.6%

Lösungsmittel

nitrobenzene

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITAfter 3 days
2. 2
   Temperaturthe mixture was heated at 95° C. to 120° C. for 1 hour
3. 3
   Temperaturcooled to 5° C.
4. 4
   Sonstigequenched with a mixture of ice (15 g), water (8 mL), and concentrated hydrochloric acid (HCl) solution (8 mL)
5. 5
   workup.ADDITIONAdditional water (150 mL) was added
6. 6
   WaschenThe ethyl acetate layer was washed with 0.2 M HCl
7. 7
   Extraktionextracted with saturated aqueous sodium bicarbonate solution
8. 8
   SonstigeThe bicarbonate layer was rotary evaporated briefly
9. 9
   Sonstigeto remove residual ethyl acetate
10. 10
    workup.ADDITIONacidified by the dropwise addition of concentrated HCl solution
11. 11
    FiltrationThe resulting tan precipitate was filtered off
12. 12
    Waschenwashed with 0.2 M HCl, and air
13. 13
    Sonstigedried
14. 14
    workup.DISSOLUTIONThe solids were dissolved in hot toluene/acetone
15. 15
    Filtrationfiltered hot through celite
16. 16
    EinengenThe filtrate was concentrated
17. 17
    Filtrationthe resulting crystals were filtered
18. 18
    Waschenwashed
19. 19
    Sonstigedried in vacuo

Vorschrift

A suspension of 4-chlorobiphenyl (9.43 g, 0.0500 mol), succinic anhydride (5.50 g, 0.0550 mol), and anhydrous aluminum chloride (14.8 g, 0.111 mol) in nitrobenzene (25 mL) at 5° C. under nitrogen was stirred 4 hours, then allowed to warm to room temperature. After 3 days, the mixture was heated at 95° C. to 120° C. for 1 hour, cooled to 5° C., and quenched with a mixture of ice (15 g), water (8 mL), and concentrated hydrochloric acid (HCl) solution (8 mL). Additional water (150 mL) was added, followed by ethyl acetate. The ethyl acetate layer was washed with 0.2 M HCl and extracted with saturated aqueous sodium bicarbonate solution. The bicarbonate layer was rotary evaporated briefly to remove residual ethyl acetate, then acidified by the dropwise addition of concentrated HCl solution. The resulting tan precipitate was filtered off, washed with 0.2 M HCl, and air dried. The solids were dissolved in hot toluene/acetone, and the solution was decolorized with activated carbon, and filtered hot through celite. The filtrate was concentrated, and the resulting crystals were filtered, washed, and dried in vacuo to give 1.96 g of 4-(4′-chloro-biphenyl-4-yl)-4-oxo-butyric acid as pale yellow plates; mp 184-185° C.

Quelle