Phthalic Anhydride → 2-(4-Isopropylbenzoyl)benzoic acid

HRID 54865Notes

Reaction equation

HRID 54865 reaction equation
[C:1]1(=[O:11])[O:6][C:4](=[O:5])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[Cl-].[Al+3].[Cl-].[Cl-].[CH:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([CH3:18])[CH3:17].C([O-])([O-])=O.[Na+].[Na+]>C(=S)=S>[CH:16]([C:19]1[CH:24]=[CH:23][C:22]([C:4]([C:3]2[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=2[C:1]([OH:6])=[O:11])=[O:5])=[CH:21][CH:20]=1)([CH3:18])[CH3:17]

Participants

6

Reactant 4

HCID 6811Phthalic AnhydrideHCID 7406CumeneHCID 10340Sodium CarbonateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 3457982-(4-Isopropylbenzoyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-9a2b4ad822004b2db735e8a8cd072b2a
Source dataset
uspto-grants-1997_04
Patent number
US05624543

Reaction notes

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