Succinic anhydride → HCID 14116665, compound

HRID 1979132Notes

Reaction equation

HRID 1979132 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[C:14]1(=[O:20])[O:19][C:17](=[O:18])[CH2:16][CH2:15]1.[Cl-].[Al+3].[Cl-].[Cl-]>[N+](C1C=CC=CC=1)([O-])=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14](=[O:20])[CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7922Succinic anhydrideHCID 163234-ChlorobiphenylHCID 6451240Aluminum(III) Chloride

Product 1

HCID 14116665HCID 14116665, compoundYield 13.6%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Procedure

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.

Workup

  1. waitAfter 3 days
  2. temperaturethe mixture was heated at 95° C. to 120° C. for 1 hour
  3. temperaturecooled to 5° C.
  4. customquenched with a mixture of ice (15 g), water (8 mL), and concentrated hydrochloric acid (HCl) solution (8 mL)
  5. additionAdditional water (150 mL) was added
  6. washThe ethyl acetate layer was washed with 0.2 M HCl
  7. extractionextracted with saturated aqueous sodium bicarbonate solution
  8. customThe bicarbonate layer was rotary evaporated briefly
  9. customto remove residual ethyl acetate
  10. additionacidified by the dropwise addition of concentrated HCl solution
  11. filtrationThe resulting tan precipitate was filtered off
  12. washwashed with 0.2 M HCl, and air
  13. customdried
  14. dissolutionThe solids were dissolved in hot toluene/acetone
  15. filtrationfiltered hot through celite
  16. concentrationThe filtrate was concentrated
  17. filtrationthe resulting crystals were filtered
  18. washwashed
  19. customdried in vacuo

Sources & evidence

ORD record
ord-1aed3af9424243b893d95205039d4f7a
Source dataset
uspto-grants-2001_05
Patent number
US06239288B1

Reaction notes

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