O-Cresol → Anthranilic Acid

HRID 971950Notes

Reaction equation

HRID 971950 reaction equation
[C:1]12[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH:6]C(=O)[O:4][C:2]2=[O:3].CC1C(O)=CC=CC=1.C1C(O)=CC=CC=1C.[OH-].[Na+]>O.O1CCOCC1>[C:2]([OH:4])(=[O:3])[C:1]1[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH2:6]

Participants

7

Reactant 4

HCID 335O-CresolHCID 342M-CresolHCID 8359Isatoic AnhydrideHCID 14798Sodium Hydroxide2×

Product 1

HCID 227Anthranilic Acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 19.2 parts of isatoic anhydride, 13.8 parts of cresylic acid (a mixture of phenols of which the main constituent is m-cresol), 0.5 parts of sodium hydroxide and 50 parts of dioxan are heated at 45°-50° C. for 4 hours. Residual sodium hydroxide is screened off and 500 parts of water are added to the filtrates. The brown oil which is formed is extracted into ether and the ether extract is washed three times with water. The ether solution is dried over magnesium sulphate and the ether is then distilled off leaving the cresylic acid ester of anthranilic acid as a brown oil.

Workup

  1. temperatureare heated at 45°-50° C. for 4 hours
  2. customThe brown oil which is formed
  3. extractionis extracted into ether
  4. extractionthe ether extract
  5. washis washed three times with water
  6. dry with materialThe ether solution is dried over magnesium sulphate
  7. distillationthe ether is then distilled off

Sources & evidence

ORD record
ord-3966e54761c345d9965b732472e6df38
Source dataset
uspto-grants-1979_07
Patent number
US04162249

Reaction notes

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