Hydrochloric Acid → 2-(4-Fluorobenzoyl)benzoic acid

HRID 846765Notes

Reaction equation

HRID 846765 reaction equation
[C:1]1(=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](=[O:10])[O:2]1.[F:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl>>[F:12][C:13]1[CH:18]=[CH:17][C:16]([C:1]([C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[C:3]([OH:2])=[O:10])=[O:11])=[CH:15][CH:14]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 6811Phthalic AnhydrideHCID 10008FluorobenzeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 820992-(4-Fluorobenzoyl)benzoic acidYield 80.7%

Procedure

To a stirred mixture of 25 parts of 1,3-isobenzofurandione and 108.5 parts of fluorobenzene were added portionwise 50 parts of aluminium chloride. Upon completion, the whole was heated slowly to reflux and stirring was continued for 1.50 hours at reflux temperature. The reaction mixture was cooled and poured onto a mixture of crushed ice and 60 parts of concentrated hydrochloric acid. The product was extracted twice with dichloromethane. The combined extracts were washed with a sodium hydroxide solution 10%. The aqueous phase was separated, washed with 2,2'-oxybispropane and acidified with concentrated hydrochloric acid while cooling. The whole was stirred for 1 hour at room temperature. The precipitated product was filtered off and dissolved in benzene. The solution was distilled azeotropically to dry. The solid residue was stired in hexane. The product was filtered off and dried in vacuo at about 50° C., yielding 33.5 parts (80.7%) of 2-(4-fluorobenzoyl)-benzoic acid; mp. 129.2° C. (intermediate 90).

Workup

  1. temperatureUpon completion, the whole was heated slowly
  2. temperatureto reflux
  3. temperatureat reflux temperature
  4. temperatureThe reaction mixture was cooled
  5. extractionThe product was extracted twice with dichloromethane
  6. washThe combined extracts were washed with a sodium hydroxide solution 10%
  7. customThe aqueous phase was separated
  8. washwashed with 2,2'-oxybispropane
  9. temperaturewhile cooling
  10. stirringThe whole was stirred for 1 hour at room temperature
  11. filtrationThe precipitated product was filtered off
  12. dissolutiondissolved in benzene
  13. distillationThe solution was distilled azeotropically
  14. customto dry
  15. filtrationThe product was filtered off
  16. customdried in vacuo at about 50° C.

Sources & evidence

ORD record
ord-5bf52c42b4254209beb3ab66e6833ab9
Source dataset
uspto-grants-1992_08
Patent number
US05137896

Reaction notes

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