Reaktion #83143

Reaktionsgleichung

Na2CO3

phthalic anhydride

aluminum chloride

isopropylbenzene

→

2-(4'-Isopropyl benzoyl)benzoic acid

Lösungsmittel

carbon disulfide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas refluxed for 7 h in a water bath
2. 2
   SonstigeThe carbon sulfide was then removed by distillation
3. 3
   workup.ADDITIONA dilute HCl solution (100 mL, 1.2N) was then added slowly to the remaining residue
4. 4
   SonstigeThe aqueous phase was decanted
5. 5
   Sonstigeto yield a sticky solid
6. 6
   Sonstigeresulted in considerable foaming
7. 7
   TemperaturThe solution was heated
8. 8
   Filtrationthe resultant solution was filtered
9. 9
   Sonstigeto remove the undissolved material
10. 10
    Sonstigeto give an oily layer which
11. 11
    Extraktionwas extracted with diethylether
12. 12
    TrocknenThe diethylether layer was dried with MgSO4
13. 13
    Filtrationfiltered
14. 14
    Sonstigethe diethylether was removed by rotary evaporation
15. 15
    Sonstigeto yield a cream-colored solid
16. 16
    SonstigeThe product was recrystallized from a 33/66 (v/v) mixture of toluene and pentane (17 g, 64%) mp 126°-127° C.

Vorschrift

A mixture of 16 g (0.11 mol) phthalic anhydride, 30 g (0.22 mol) aluminum chloride and 12 g (0.10 mol) isopropylbenzene in 120 mL carbon disulfide was refluxed for 7 h in a water bath. The carbon sulfide was then removed by distillation. A dilute HCl solution (100 mL, 1.2N) was then added slowly to the remaining residue. The aqueous phase was decanted to yield a sticky solid. Na2CO3 aqueous solution (500 mL, 15%) was added slowly to the residue which resulted in considerable foaming. The solution was heated and the resultant solution was filtered to remove the undissolved material. The filtrate was acidified with conc. HCl to give an oily layer which was extracted with diethylether. The diethylether layer was dried with MgSO4, filtered and then the diethylether was removed by rotary evaporation to yield a cream-colored solid. The product was recrystallized from a 33/66 (v/v) mixture of toluene and pentane (17 g, 64%) mp 126°-127° C.

Quelle