4-Nitrobenzaldehyde → HCID 67897623, compound

HRID 2373095Notes

Reaction equation

HRID 2373095 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=O)[CH3:13].[OH-:21].[Na+]>C(O)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH:8]([OH:9])[C:13](=[O:21])[CH2:12][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:10][CH:11]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 5414-NitrobenzaldehydeHCID 7410AcetophenoneHCID 14798Sodium Hydroxide

Product 1

HCID 67897623HCID 67897623, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

p-Nitrobenzaldehyde is reacted with acetophenone and sodium hydroxide in ethanol to produce 3-(p-nitrophenyl)-3-hydroxy-1-phenyl propanone. The resulting compound is reacted with KHSO4 to obtain p-nitrochalcone. p-Nitrochalcone is hydrogenated in the presence of platinum catalyst to produce 3-(p-aminophenyl)-1-phenyl propanone. The resulting compound is reacted with potassium hydroxide and hydrazine in triethylene glycol to produce p-aminodiophenylpropane. p-Aminodiphenylpropane is reacted with fuming nitric acid and acetic acid anhydride to obtain 1-(p-aminophenyl)-3-p-nitrophenyl)-propane.

Sources & evidence

ORD record
ord-6d8e349132af4092a25fed2614f888b7
Source dataset
uspto-grants-1992_03
Patent number
US05101411

Reaction notes

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