Hydrochloric Acid → 4,4'-(Ethene-1,1-diyl)bis(N,N-diethylaniline)

HRID 1199115Notes

Reaction equation

HRID 1199115 reaction equation
Cl.[CH2:2]([N:4]([CH2:27][CH3:28])[C:5]1[CH:10]=[CH:9][C:8]([C:11]([C:16]2[CH:21]=[CH:20][C:19]([N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[CH:18][CH:17]=2)(C)[C:12](O)=O)=[CH:7][CH:6]=1)[CH3:3].[OH-].[Na+]>>[CH2:25]([N:22]([CH2:23][CH3:24])[C:19]1[CH:20]=[CH:21][C:16]([C:11]([C:8]2[CH:7]=[CH:6][C:5]([N:4]([CH2:27][CH3:28])[CH2:2][CH3:3])=[CH:10][CH:9]=2)=[CH2:12])=[CH:17][CH:18]=1)[CH3:26]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 14227880HCID 14227880, compound

Product 1

HCID 2478774,4'-(Ethene-1,1-diyl)bis(N,N-diethylaniline)Yield 74.3%

Procedure

Into 200 ml of IN--HCl solution was dissolved 10 g of 2,2-bis(4-diethylaminophenyl)propionic acid. Thereto was gradually added 5.7 g of ferric chloride at room temperature and the mixture was reacted with stirring for 2 hours. The reaction mixture was adjusted to alkaline with addition of aqueous solution of sodium hydroxide and then extracted with 50 ml of toluene. The toluene layer was concentrated at a reduced pressure to obtain crystals. The crystal was recrystallized from ethanol to give 6.5 g (yield 74.3%) of 1,1-bis(4-diethylaminophenyl)ethylene, having a melting point of 100°~102° C.

Workup

  1. customat room temperature
  2. customthe mixture was reacted
  3. extractionextracted with 50 ml of toluene
  4. concentrationThe toluene layer was concentrated at a reduced pressure
  5. customto obtain crystals
  6. customThe crystal was recrystallized from ethanol

Sources & evidence

ORD record
ord-6f605799c28e40e9bf5628a385e7dd55
Source dataset
uspto-grants-1990_02
Patent number
US04898941

Reaction notes

Loading…