Phthalic Anhydride → O-(p-Anisoyl)benzoic acid

HRID 414154Notes

Reaction equation

HRID 414154 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]1(=[O:15])[O:10][C:8](=[O:9])[C:7]2=[CH:11][CH:12]=[CH:13][CH:14]=[C:6]12.[C:16]1([O:22][CH3:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(=S)=S>[CH3:23][O:22][C:16]1[CH:21]=[CH:20][C:19]([C:8]([C:7]2[CH:11]=[CH:12][CH:13]=[CH:14][C:6]=2[C:5]([OH:10])=[O:15])=[O:9])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 6811Phthalic AnhydrideHCID 7519AnisoleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 231963O-(p-Anisoyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

Anhydrous aluminum chloride (140 g) was added at ambient temperature to a vigorously stirred mixture of 148 g of phthalic anhydride, 250 ml anisole, and 250 ml carbon disulfide. After 2.5 hours, the solution was hydrolyzed with ice water and the organic solvents were removed by steam distillation. A gray solid which precipitated when the residual solution cooled to room temperature was separated from the liquid by decantation and dissolved in ca. 1 L chloroform. Rotary evaporation of the chloroform left 107 g (42%) of white solid which was recrystallized from acetic acid/water: mp. 142°-144.5° C. (lit.* mp. 122°-123.5° C.). IR (KBr): 1686, 1660 (two different carbonyls), 1550-1600, 1420-1370, 1280, 1255, 1170, 1150, 1015, 850, 800, 755 cm-1.

Workup

  1. customthe organic solvents were removed by steam distillation
  2. customA gray solid which precipitated when the residual solution
  3. customwas separated from the liquid by decantation
  4. dissolutiondissolved in ca. 1 L chloroform
  5. customRotary evaporation of the chloroform
  6. waitleft 107 g (42%) of white solid which
  7. customwas recrystallized from acetic acid/water

Sources & evidence

ORD record
ord-a4e43a929d5a4400a026c19ae055c9d7
Source dataset
uspto-grants-1988_12
Patent number
US04790961

Reaction notes

Loading…