تفاعل #468996

معادلة التفاعل

4-chlorobiphenyl

succinic anhydride

aluminum chloride

→

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

المردود 13.6%

المذيبات

nitrobenzene

ظروف التفاعل

المعالجة

1. 1
   workup.WAITAfter 3 days
2. 2
   درجة الحرارةthe mixture was heated at 95° C. to 120° C. for 1 hour
3. 3
   درجة الحرارةcooled to 5° C.
4. 4
   أخرىquenched 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
   غسيلThe ethyl acetate layer was washed with 0.2 M HCl
7. 7
   استخلاصextracted with saturated aqueous sodium bicarbonate solution
8. 8
   أخرىThe bicarbonate layer was rotary evaporated briefly
9. 9
   أخرىto remove residual ethyl acetate
10. 10
    workup.ADDITIONacidified by the dropwise addition of concentrated HCl solution
11. 11
    ترشيحThe resulting tan precipitate was filtered off
12. 12
    غسيلwashed with 0.2 M HCl, and air
13. 13
    أخرىdried
14. 14
    workup.DISSOLUTIONThe solids were dissolved in hot toluene/acetone
15. 15
    ترشيحfiltered hot through celite
16. 16
    تركيزThe filtrate was concentrated
17. 17
    ترشيحthe resulting crystals were filtered
18. 18
    غسيلwashed
19. 19
    أخرىdried in vacuo

الإجراء التجريبي

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.

المصدر