Maleic Anhydride → Phthalic Acid

HRID 971452Notes

Reaction equation

HRID 971452 reaction equation
[N+]([C:4]1[CH:5]=[C:6]([C:13]([OH:15])=[O:14])[C:7](=[CH:11][CH:12]=1)[C:8]([OH:10])=[O:9])([O-])=O.C1(=O)OC(=O)C=C1>O1CCOCC1.[Pd]>[C:13]([OH:15])(=[O:14])[C:6]1[C:7](=[CH:11][CH:12]=[CH:4][CH:5]=1)[C:8]([OH:10])=[O:9]

Participants

5

Reactant 2

HCID 7923Maleic AnhydrideHCID 691211,2-Benzenedicarboxylic acid, 4-nitro-

Product 1

HCID 1017Phthalic Acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 312751,4-DioxaneSolvent

Procedure

84.5 g (0.4 mol) of 4-nitrophthalic acid are hydrogenated in 720 ml of dioxane, in the presence of 4 g of a palladium/charcoal catalyst containing 5% by weight of palladium, at 25° C. 47.02 g (0.48 mol) of maleic anhydride are added to the filtered reaction solution. After a reaction time of 12 hours, the 4-(maleinamidyl)-phthalic acid which has precipitated is filtered off and washed with 50 ml of dioxane. After drying at 80° C./15 mm Hg for 12 hours, 101.6 g (91% of theory) of 4-maleinamidyl)-phthalic acid are obtained.

Workup

  1. customat 25° C
  2. customAfter a reaction time of 12 hours, the 4-(maleinamidyl)-phthalic acid which has precipitated
  3. filtrationis filtered off
  4. washwashed with 50 ml of dioxane
  5. customAfter drying at 80° C./15 mm Hg for 12 hours

Sources & evidence

ORD record
ord-1ef9c02ef3ac46f49416198c41982fd7
Source dataset
uspto-grants-1979_07
Patent number
US04160081

Reaction notes

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