Glutaric anhydride → 4-(4-Fluorobenzoyl)butyric Acid

HRID 1052888Notes

Reaction equation

HRID 1052888 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[F:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:12]1(=[O:19])[O:18][C:16](=[O:17])[CH2:15][CH2:14][CH2:13]1>ClCCl>[F:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:19])[CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 7940Glutaric anhydrideHCID 10008Fluorobenzene2×HCID 6451240Aluminum(III) Chloride

Product 1

HCID 6890964-(4-Fluorobenzoyl)butyric Acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

25 gms of Aluminium chloride was added to 50 ml of dichloromethane and 4.5 ml of fluorobenzene. To this a solution of 50 ml of dichloromethane containing 10 gms of glutaric anhydride and 4.5 ml of fluorobenzene was added. Reaction mass was stirred at room temperature. After completion of reaction, reaction mass was quenched with ice & HCl solution at 0-10° C. Filtered the reaction mass. The obtained wet solid was dissolved in aq NaHCO3 solution at 60-70° C. and insoluable material was filtered. Cooled the filtrate and adjust pH to 2.0 by adding hydrochloric acid. Obtained solid was filtered and dried at 60-70° C. under vacuum to get 10 gm of 5-(4-Fluoro-phenyl)-5-oxo-pentanoic acid.

Workup

  1. customReaction mass
  2. customAfter completion of reaction, reaction mass
  3. customwas quenched with ice & HCl solution at 0-10° C
  4. filtrationFiltered the reaction mass
  5. dissolutionThe obtained wet solid was dissolved in aq NaHCO3 solution at 60-70° C.
  6. filtrationinsoluable material was filtered
  7. temperatureCooled the filtrate
  8. additionby adding hydrochloric acid
  9. customObtained solid
  10. filtrationwas filtered
  11. customdried at 60-70° C. under vacuum

Sources & evidence

ORD record
ord-74396afbf83f401b94718b6bfaccffc5
Source dataset
uspto-grants-2016_07
Patent number
US09388440B2

Reaction notes

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