Potassium Carbonate → 4,4'-Oxydiphthalic acid

HRID 465738Notes

Reaction equation

HRID 465738 reaction equation
ClC1C=C2C(=O)OC(=[O:7])C2=CC=1.C([O-])(=O)C1C=CC=CC=1.[K+].[C:23](=[O:26])([O-:25])[O-].[K+].[K+].[CH:29]1[C:34]([O:35][C:36]2[CH:41]=[CH:40][C:39]3C([O:44][C:45](=[O:46])[C:38]=3[CH:37]=2)=O)=[CH:33][C:32]2[C:47]([O:49][C:50](=[O:51])[C:31]=2[CH:30]=1)=[O:48]>CN1CCCC1=O>[O:35]([C:36]1[CH:37]=[C:38]([C:45]([OH:44])=[O:46])[C:39](=[CH:40][CH:41]=1)[C:23]([OH:25])=[O:26])[C:34]1[CH:33]=[C:32]([C:47]([OH:49])=[O:48])[C:31](=[CH:30][CH:29]=1)[C:50]([OH:51])=[O:7]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 670444-Chlorophthalic anhydrideHCID 745744,4'-Oxydiphthalic anhydrideHCID 23661960Potassium Benzoate

Product 1

HCID 821364,4'-Oxydiphthalic acid

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

4-Chlorophthalic anhydride (10 g, 55 mmol), potassium benzoate (1.0 g, 6.2 mmol), and N-methylpyrrolidinone (25 g) were heated to about 175.C. Potassium carbonate (3.87 g, 28 mmol) was added and the suspension was heated to about 175.C. After 2 hours, GC analysis indicated a greater than 97% conversion to 4,4'-oxydiphthalic anhydride. The solvent was removed under reduced pressure and the residue treated with an aqueous 25% sodium hydroxide solution. The solution was acidified with concentrated HCl. The solid was collected and dried to give 4,4'-oxydiphthalic acid (4.85 g) mixed with some sodium chloride. The tetra acid was cyclized and recrystallized from hot acetic anhydride (2.4 mL) and filtered to remove salts to give 4,4'-oxydiphthalic anhydride, 4.2 g.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionthe residue treated with an aqueous 25% sodium hydroxide solution
  3. customThe solid was collected
  4. customdried

Sources & evidence

ORD record
ord-ac749a465ea34eb891d05bb60c6e6e70
Source dataset
uspto-grants-1992_10
Patent number
US05153335

Reaction notes

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