Hydrochloric Acid → 4,4′-Cyclohexylidenebis[benzenamine]

HRID 375667Notes

Reaction equation

HRID 375667 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[C:9]1(=O)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.[OH-].[Na+]>>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:9]2([C:5]3[CH:6]=[CH:7][C:2]([NH2:1])=[CH:3][CH:4]=3)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 6115AnilineHCID 7967CyclohexanoneHCID 14798Sodium Hydroxide

Product 1

HCID 7683254,4′-Cyclohexylidenebis[benzenamine]

Procedure

240 Parts of aniline is mixed with 240 parts of hydrochloric acid with stirring, and then 75 parts of cyclohexanone is added to the mixture, which is subjected to the condensation reaction with stirring at 102° to 108° C. for about 24 hours. Then, 700 parts of a 45% aqueous sodium hydroxide solution is added and the non-reacted aniline is collected by steam distillation. Thereafter, 1,1-bis(4-aminophenyl)cyclohexane can be obtained as a crude solid by cooling. In the preferred embodiment of the present invention, this intermediate was purified from solvent to afford a high-purity product, which was used.

Workup

  1. customis subjected to the condensation reaction
  2. stirringwith stirring at 102° to 108° C. for about 24 hours
  3. distillationthe non-reacted aniline is collected by steam distillation

Sources & evidence

ORD record
ord-7fe63a56f6544a4e87806b1c59809277
Source dataset
uspto-grants-1996_01
Patent number
US05486601

Reaction notes

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