Water → HCID 22316031, compound

HRID 1769838Notes

Reaction equation

HRID 1769838 reaction equation
[N+:1]([C:4]1[CH:38]=[CH:37][C:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3([C:21]4[CH:26]=[CH:25][C:24]([CH2:27][C:28]5[CH:33]=[CH:32][C:31]([N+:34]([O-])=O)=[CH:30][CH:29]=5)=[CH:23][CH:22]=4)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)=[CH:11][CH:10]=2)=[CH:6][CH:5]=1)([O-])=O.O.[H][H]>O1CCCC1>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([C:15]3([C:21]4[CH:26]=[CH:25][C:24]([CH2:27][C:28]5[CH:29]=[CH:30][C:31]([NH2:34])=[CH:32][CH:33]=5)=[CH:23][CH:22]=4)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)=[CH:13][CH:14]=2)=[CH:37][CH:38]=1

Participants

5

Reactant 3

HCID 962WaterHCID 20097777HCID 20097777, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22316031HCID 22316031, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,1-bis[4-(4-nitrobenzyl)phenyl]cyclohexane 98.93 g was dissolved in 1100 ml of tetrahydrofuran, a Pd--C catalyst (5% purity, water content 55.9%) 9.8 g was added, and the mixture was cooled with water at atmospheric pressure and contacted with hydrogen gas with stirring. After the absorption of hydrogen stopped, the catalyst was filtered off and the solution was concentrated. The concentrate was recrystallized with toluene solvent to obtain 71.71 g of 1,1-bis[4-(4aminobenzyl)phenyl]cyclohexane which is a diamino compound of the present invention. The melting point was 154.4°-155.5° C.

Workup

  1. customAfter the absorption of hydrogen
  2. filtrationthe catalyst was filtered off
  3. concentrationthe solution was concentrated
  4. customThe concentrate was recrystallized with toluene solvent

Sources & evidence

ORD record
ord-fdff7bb0d44849069a8d5bd6b4b00452
Source dataset
uspto-grants-1995_01
Patent number
US05382688

Reaction notes

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