Water → HCID 20366403, compound

HRID 616873Notes

Reaction equation

HRID 616873 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([CH3:10])=[CH:4][C:3]=1[O:11][CH3:12].N1C=CC=CC=1.[Mn]([O-])(=O)(=O)=[O:20].[K+].[OH2:25]>>[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([C:10]([OH:20])=[O:25])=[CH:4][C:3]=1[O:11][CH3:12]

Participants

5

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 516875Potassium PermanganateHCID 139393492-Chloro-1,3-dimethoxy-5-methylbenzene

Product 1

HCID 20366403HCID 20366403, compound

Procedure

77.5 G. of 4-chloro-3,5-dimethoxytoluene were dissolved in 1030 ml. of pyridine. The solution was heated to reflux and treated dropwise during 1 hour with a solution of 197 g. of potassium permanganate in 3100 ml. of hot water. The mixture was heated to reflux for an additional 30 minutes. Then, 1700 ml. of a pyridine/water mixture were recovered by distillation. The residue was removed by filtration under suction while hot and, after cooling, the filtrate was acidified with 600 ml. of 10N sulfuric acid. The precipitate was removed by filtration and extracted with ether to recover unreacted starting material, whereby there was obtained 4-chloro-3,5-dimethoxybenzoic acid having a melting point of 247° C.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux
  3. additiontreated dropwise during 1 hour with a solution of 197 g
  4. temperatureThe mixture was heated
  5. temperatureto reflux for an additional 30 minutes
  6. distillationof a pyridine/water mixture were recovered by distillation
  7. customThe residue was removed by filtration under suction while hot and,
  8. temperatureafter cooling
  9. customThe precipitate was removed by filtration
  10. extractionextracted with ether
  11. customto recover unreacted

Sources & evidence

ORD record
ord-4b2b4edd535a47ca85da314b9cf78688
Source dataset
uspto-grants-1978_02
Patent number
US04076810

Reaction notes

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