Lead dioxide → 1,1-Bis(4-pyrrolidinophenyl)ethylene

HRID 1199112Notes

Reaction equation

HRID 1199112 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([C:12]([C:17]3[CH:22]=[CH:21][C:20]([N:23]4[CH2:27][CH2:26][CH2:25][CH2:24]4)=[CH:19][CH:18]=3)(C)[C:13](O)=O)=[CH:8][CH:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[Pb](=O)=O>C1(C)C=CC=CC=1>[N:1]1([C:6]2[CH:7]=[CH:8][C:9]([C:12]([C:17]3[CH:22]=[CH:21][C:20]([N:23]4[CH2:24][CH2:25][CH2:26][CH2:27]4)=[CH:19][CH:18]=3)=[CH2:13])=[CH:10][CH:11]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 14793Lead dioxideHCID 142278762,2-Bis(4-pyrrolidinophenyl)propionic acid

Product 1

HCID 32960211,1-Bis(4-pyrrolidinophenyl)ethyleneYield 76%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Into 500 ml of toluene was dissolved 5 g of 2,2-bis(4-pyrrolidinophenyl)propionic acid. Thereto was added 3.7 g of lead dioxide and the mixture was reacted at room temperature with stirring for one hour. The lead compound was removed by filtration and the toluene layer was washed with 100 ml of 5% aqueous solution of sodium hydroxide. Toluene was removed by distillation at a reduced pressure. The residue was recrystallized from ethanol to obtain 3.3 g (yield 76%) of 1,1-bis(4-pyrrolidinophenyl)ethylene, having a melting point of 220°~223° C.

Workup

  1. customthe mixture was reacted at room temperature
  2. customThe lead compound was removed by filtration
  3. washthe toluene layer was washed with 100 ml of 5% aqueous solution of sodium hydroxide
  4. customToluene was removed by distillation at a reduced pressure
  5. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-c665e68ab54e4aab89154d65cf69bff5
Source dataset
uspto-grants-1990_02
Patent number
US04898941

Reaction notes

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