Hydrogen Peroxide → 1-{4-[1-(4-Methoxyphenyl)ethenyl]phenyl}pyrrolidine

HRID 1199114Notes

Reaction equation

HRID 1199114 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([C:16]2[CH:21]=[CH:20][C:19]([N:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)=[CH:18][CH:17]=2)(C)[C:12](O)=O)=[CH:7][CH:6]=1.OO>>[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([C:16]2[CH:21]=[CH:20][C:19]([N:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)=[CH:18][CH:17]=2)=[CH2:12])=[CH:7][CH:6]=1

Participants

4

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 19868034HCID 19868034, compound

Product 1

HCID 143237921-{4-[1-(4-Methoxyphenyl)ethenyl]phenyl}pyrrolidineYield 69.9%

Procedure

Into 50 ml of 5% aqueous solution of sodium hydroxide was dissolved 5 g of 2-(4-methoxyphenyl)-2-(4-pyrrolidinophenyl)propionic acid. Thereto was gradually added dropwise 2.4 g of 35% aqeous solution of hydrogen peroxide and the mixture was reacted at room temperature with stirring for 2 hours, and further at 60° C. with stirring for one hour. The reaction mixture was cooled and the precipitated crystal was collected by filtration. The crystal was recrystallized from methanol to give 3.0 g (yield 69.9%) of 1-(4-methoxyphenyl)-1-(4-pyrrolidinophenyl)ethylene, having a melting point of 159°~162° C.

Workup

  1. customthe mixture was reacted at room temperature
  2. stirringfurther at 60° C. with stirring for one hour
  3. temperatureThe reaction mixture was cooled
  4. filtrationthe precipitated crystal was collected by filtration
  5. customThe crystal was recrystallized from methanol

Sources & evidence

ORD record
ord-ed73a16bc8784b1db4b579dfac80fc5e
Source dataset
uspto-grants-1990_02
Patent number
US04898941

Reaction notes

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