Water → 4-Chlorophthalic acid

HRID 2398564Notes

Reaction equation

HRID 2398564 reaction equation
ClC1C=C(C)C(C)=CC=1.[Mn]([O-])(=O)(=O)=[O:11].[K+].NC1C=CC(C)=C(N2[C:28](=[O:29])[C:27]3=[CH:30][C:31]([Cl:34])=[CH:32][CH:33]=[C:26]3[C:25]2=[O:35])C=1.[OH2:36]>>[Cl:34][C:31]1[CH:30]=[C:27]([C:28]([OH:29])=[O:11])[C:26](=[CH:33][CH:32]=1)[C:25]([OH:35])=[O:36]

Participants

5

Reactant 4

HCID 962WaterHCID 328864-Chloro-o-xyleneHCID 516875Potassium PermanganateHCID 70621330HCID 70621330, compound

Product 1

HCID 69644-Chlorophthalic acid

Procedure

The starting material is prepared as follows: The mixture of 9.0 g of 4-chloro-o-xylene and the solution of 60.7 g of potassium permanganate in 280 ml of water is refluxed until the purple color disappears (about 7 hours) whereupon 3/4 of the water are distilled off and the remaining suspension is filtered while still hot. The residue is washed with hot water several times, the clear and colorless filtrate (pH~12) is concentrated to about 50 ml and acidified with 33 ml of concentrated hydrochloric acid. The cold mixture is extracted 3 times with ethyl acetate, the organic layer dried and evaporated to give the 4-chlorophthalic acid.

Workup

  1. customThe starting material is prepared
  2. custom(about 7 hours)
  3. distillationare distilled off
  4. filtrationthe remaining suspension is filtered while still hot
  5. washThe residue is washed with hot water several times
  6. concentrationthe clear and colorless filtrate (pH~12) is concentrated to about 50 ml
  7. extractionThe cold mixture is extracted 3 times with ethyl acetate
  8. customthe organic layer dried
  9. customevaporated

Sources & evidence

ORD record
ord-d7977e7a38194e18975fe80a54bc6260
Source dataset
uspto-grants-1977_05
Patent number
US04025505

Reaction notes

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