2,2-Bis(4-nitrophenyl)propane → 4,4'-Isopropylidenedianiline

HRID 1107995

Reaction equation

HRID 1107995 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=2)([CH3:12])[CH3:11])=[CH:6][CH:5]=1)([O-])=O>[Pd].O1CCOCC1>[C:10]([C:13]1[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=1)([C:7]1[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=1)([CH3:12])[CH3:11]

Participants

4

Reactant 1

HCID 40759292,2-Bis(4-nitrophenyl)propane

Product 1

HCID 755914,4'-IsopropylidenedianilineYield 96.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 294 g of 2,2-bis(4-nitrophenyl)propane (1.03 mol; prepared as in step c) was charged in an autoclave along with 2 liters of 1,4-dioxane and 25 g of 5% palladium on carbon. The autoclave was purged with nitrogen, then heated at 60° C. for six hours under 500 psi hydrogen pressure. The product mixture was filtered to remove the catalyst, then stripped of solvent by rotary evaporation at reduced pressure. The solid residue was triturated with a small amount of hexane, then collected and dried by suction filtration under a blanket of nitrogen to afford 224.0 g (0.99 mol, 96% of theory) of 4,4'-isopropylidenedianiline (bisaniline-A), m.p. 130-131.5° C.

Workup

  1. customThe autoclave was purged with nitrogen
  2. filtrationThe product mixture was filtered
  3. customto remove the catalyst
  4. customstripped of solvent by rotary evaporation at reduced pressure
  5. customThe solid residue was triturated with a small amount of hexane
  6. customcollected
  7. customdried by suction filtration under a blanket of nitrogen

Sources & evidence

ORD record
ord-32d861896b04469c97915ba0da804b9f
Source dataset
uspto-grants-2000_05
Patent number
US06063892

Linked notes

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