Phenol → 3,5-Dichloroaniline

HRID 1462646Notes

Reaction equation

HRID 1462646 reaction equation
Cl[C:2]1[C:8]([Cl:9])=[C:7](Cl)[C:6]([Cl:11])=[CH:5][C:3]=1[NH2:4].C1(O)C=CC=CC=1.[OH-].[Na+]>[Pd].[H][H].O.C1(C)C=CC=CC=1.[Ta]>[Cl:9][C:8]1[CH:2]=[C:3]([CH:5]=[C:6]([Cl:11])[CH:7]=1)[NH2:4]

Participants

9

Reactant 3

HCID 996PhenolHCID 124662,3,4,5-TetrachloroanilineHCID 14798Sodium Hydroxide

Product 1

HCID 122813,5-Dichloroaniline

Reagents, catalysts & solvents 5

HCID 23938PalladiumCatalystHCID 23956TantalumCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

40 parts of 2,3,4,5-tetrachloroaniline, 150 parts of phenol and 12 g of a moist palladium/charcoal catalyst already used for this reaction (1% strength, 8 g dry) are mixed, and the mixture is stirred in a tantalum autoclave for 6 hours after forcing in hydrogen up to a total pressure of from 16 to a maximum of 18 bar at 165° C. After the pressurised vessel has been cooled and the pressure released, the reaction mixture is diluted with water, toluene is added, and the mixture is rendered alkaline with sodium hydroxide solution. The catalyst is separated off by filtering under suction. The toluene phase is distilled, and 27.7 parts (=99% of yield) of 98.5% strength 3,5-dichloroaniline are obtained.

Workup

  1. additionare mixed
  2. temperatureAfter the pressurised vessel has been cooled
  3. additionis added
  4. customThe catalyst is separated off
  5. filtrationby filtering under suction
  6. distillationThe toluene phase is distilled

Sources & evidence

ORD record
ord-ffa5a5d88d5d48d69da359333e15f1a4
Source dataset
uspto-grants-1984_07
Patent number
US04460788

Reaction notes

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