4-Aminobenzoic Acid → Benzoic Acid

HRID 1290149Notes

Reaction equation

HRID 1290149 reaction equation
N[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.C1(=O)OC(=O)C=C1>CC(C)=O.CO>[C:6]([OH:8])(=[O:7])[C:5]1[CH:9]=[CH:10][CH:2]=[CH:3][CH:4]=1

Participants

5

Reactant 2

HCID 9784-Aminobenzoic AcidHCID 7923Maleic Anhydride

Product 1

HCID 243Benzoic AcidYield 163.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 887MethanolSolvent

Procedure

Solution "A" was prepared by dissolving 42.6 grams of para-aminobenzoic acid in 300 ml acetone plus 50 ml of methyl alcohol. Solution "B" was prepared by dissolving 36.6 g of maleic anhydride in 100 ml acetone. Solution "B" was added to solution "A" in one shot at room temperature with stirring. The mixture was allowed to stir for one to two hours until a yellow precipitate was formed. The precipitate was then washed with fresh acetone and dried to yield approximately 62 grams of maleamidated benzoic acid.

Workup

  1. customSolution "A" was prepared
  2. customSolution "B" was prepared
  3. additionSolution "B" was added to solution "A" in one shot at room temperature
  4. stirringto stir for one to two hours until a yellow precipitate
  5. customwas formed
  6. washThe precipitate was then washed with fresh acetone
  7. customdried

Sources & evidence

ORD record
ord-bef24dac17724f60abcd8833e6390338
Source dataset
uspto-grants-1998_05
Patent number
US05750725

Reaction notes

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