2-Chloro-6-nitrotoluene → 2-Chloro-6-nitrobenzoic acid

HRID 1995392Notes

Reaction equation

HRID 1995392 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[CH3:11].[Mn]([O-])(=O)(=O)=[O:13].[K+].[OH-:18].[K+]>O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[C:11]([OH:13])=[O:18]

Participants

5

Reactant 3

HCID 67402-Chloro-6-nitrotolueneHCID 14797Potassium HydroxideHCID 516875Potassium Permanganate2×

Product 1

HCID 792872-Chloro-6-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 77.7 gm (0.453 mol) of 2-chloro-6-nitro-toluene, 190 gm (1.2 mol) of potassium permanganate, 500 ml of 1 N potassium hydroxide and 4 liters of water was heated for 8.5 hours at 100° C. After standing overnight, 25 gm (0.16 mol) of potassium permanganate were added, and the reaction mixture was heated for 2.5 hours more at 100° C. The unreacted starting material was distilled off by steam distillation. The remaining reaction solution was filtered, the filter cake was washed with hot water, and the combined filtrates were evaporated to about 750 ml. After acidifying with hydrochloric acid a precipitate was obtained, which was filtered off and dried.

Workup

  1. temperaturethe reaction mixture was heated for 2.5 hours more at 100° C
  2. distillationwas distilled off by steam distillation
  3. customThe remaining reaction solution
  4. filtrationwas filtered
  5. washthe filter cake was washed with hot water
  6. customthe combined filtrates were evaporated to about 750 ml
  7. customwas obtained
  8. filtrationwhich was filtered off
  9. customdried

Sources & evidence

ORD record
ord-5159393199984ed08503537ee2f7d5f0
Source dataset
uspto-grants-1983_09
Patent number
US04404230

Reaction notes

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