반응 #63578

반응 방정식

hydrochloric acid

aluminium chloride

1,3-isobenzofurandione

fluorobenzene

→

2-(4-fluorobenzoyl)benzoic acid

수율 80.7%

반응 조건

후처리

1. 1
   온도Upon completion, the whole was heated slowly
2. 2
   온도to reflux
3. 3
   온도at reflux temperature
4. 4
   온도The reaction mixture was cooled
5. 5
   추출The product was extracted twice with dichloromethane
6. 6
   세척The combined extracts were washed with a sodium hydroxide solution 10%
7. 7
   기타The aqueous phase was separated
8. 8
   세척washed with 2,2'-oxybispropane
9. 9
   온도while cooling
10. 10
    workup.STIRRINGThe whole was stirred for one hour at room temperature
11. 11
    여과The precipitated product was filtered off
12. 12
    workup.DISSOLUTIONdissolved in benzene
13. 13
    workup.DISTILLATIONThe solution was distilled azeotropically
14. 14
    기타to dry
15. 15
    workup.STIRRINGThe solid residue was stirred in hexane
16. 16
    여과The product was filtered off
17. 17
    기타dried in vacuo at about 50° C.

실험 절차

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).

출처