Reaktion #63578

Reaktionsgleichung

hydrochloric acid

aluminium chloride

1,3-isobenzofurandione

fluorobenzene

→

2-(4-fluorobenzoyl)benzoic acid

Ausbeute 80.7%

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturUpon completion, the whole was heated slowly
2. 2
   Temperaturto reflux
3. 3
   Temperaturat reflux temperature
4. 4
   TemperaturThe reaction mixture was cooled
5. 5
   ExtraktionThe product was extracted twice with dichloromethane
6. 6
   WaschenThe combined extracts were washed with a sodium hydroxide solution 10%
7. 7
   SonstigeThe aqueous phase was separated
8. 8
   Waschenwashed with 2,2'-oxybispropane
9. 9
   Temperaturwhile cooling
10. 10
    workup.STIRRINGThe whole was stirred for one hour at room temperature
11. 11
    FiltrationThe precipitated product was filtered off
12. 12
    workup.DISSOLUTIONdissolved in benzene
13. 13
    workup.DISTILLATIONThe solution was distilled azeotropically
14. 14
    Sonstigeto dry
15. 15
    workup.STIRRINGThe solid residue was stirred in hexane
16. 16
    FiltrationThe product was filtered off
17. 17
    Sonstigedried in vacuo at about 50° C.

Vorschrift

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 one 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 stirred 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 7).

Quelle