Hydrochloric Acid → 3,5-Dichloroaniline

HRID 2296514Notes

Reaction equation

HRID 2296514 reaction equation
C1(O)C=CC=CC=1.ClC1C(Cl)=C(C=CC=1)N(Cl)Cl.Cl[C:20]1[C:25]([NH2:26])=[C:24](Cl)[C:23]([Cl:28])=[C:22](Cl)[C:21]=1[Cl:30].Cl.[H][H]>[Ta]>[Cl:28][C:23]1[CH:24]=[C:25]([CH:20]=[C:21]([Cl:30])[CH:22]=1)[NH2:26]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 996PhenolHCID 131713377HCID 131713377, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 122813,5-DichloroanilineYield 97%

Reagents, catalysts & solvents 1

HCID 23956TantalumCatalyst

Procedure

200 parts of phenol, 131 parts of a tetrachloroaniline/pentachloroaniline mixture corresponding to the composition mentioned in Example 3, 1 part of ruthenium-on-charcoal catalyst (5% strength) which has already been used for 10 previous similar experiments, and 12 parts of aqueous hydrochloric acid (57% strength) are reacted in a tantalum autoclave, during the course of 3.5 hours at 165° C., whilst stirring, at a hydrogen pressure of 50 bars. After the usual working up, 90 parts of 99% strength 3,5-dichloroaniline are isolated. Yield: 97% of theory.

Sources & evidence

ORD record
ord-0be853c85c9b424da3a64e0abd8023db
Source dataset
uspto-grants-1984_01
Patent number
US04429156

Reaction notes

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