Bisphenol A diglycidyl ether → 2,2-Bis[4-{2-hydroxy-3-[N-octyl-N-(2,2,6,6-tetramethyl-4-piperidyl)amino]propoxy}phenyl]propane

HRID 1862924Notes

Reaction equation

HRID 1862924 reaction equation
[CH3:1][C:2]1([CH3:19])[CH2:7][CH:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH2:5][C:4]([CH3:18])([CH3:17])[NH:3]1.[O:20]1[CH2:44][CH:21]1[CH2:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]([C:33]2[CH:38]=[CH:37][C:36]([O:39][CH2:40][CH:41]3[O:43][CH2:42]3)=[CH:35][CH:34]=2)([CH3:32])[CH3:31])=[CH:26][CH:25]=1>CO>[OH:43][CH:41]([CH2:42][N:8]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH:6]1[CH2:7][C:2]([CH3:1])([CH3:19])[NH:3][C:4]([CH3:17])([CH3:18])[CH2:5]1)[CH2:40][O:39][C:36]1[CH:37]=[CH:38][C:33]([C:30]([C:27]2[CH:28]=[CH:29][C:24]([O:23][CH2:22][CH:21]([OH:20])[CH2:44][N:8]([CH:6]3[CH2:5][C:4]([CH3:18])([CH3:17])[NH:3][C:2]([CH3:19])([CH3:1])[CH2:7]3)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[CH:25][CH:26]=2)([CH3:32])[CH3:31])=[CH:34][CH:35]=1

Participants

4

Reactant 2

HCID 2286Bisphenol A diglycidyl etherHCID 143651212,2,6,6-Tetramethyl-4-octylaminopiperidine

Product 1

HCID 203935552,2-Bis[4-{2-hydroxy-3-[N-octyl-N-(2,2,6,6-tetramethyl-4-piperidyl)amino]propoxy}phenyl]propane

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 13 g of 2,2,6,6-tetramethyl-4-octylaminopiperidine and 8 g of 2,2-bis[p-(2,3-epoxypropoxy)phenyl]propane in 200 ml of methanol was refluxed, with stirring, for 6 hours. At the end of this time, the solvent was removed from the residue by evaporation under reduced pressure, leaving a residue, which was purified by column chromatography through silica gel eluted with a 20:4:2:1 by volume mixture of ethyl acetate, benzene, ethanol and triethylamine. The desired compound was obtained in the form of a colourless, transparent, very viscous liquid having an Rf value of 0.27 on thin layer chromatography on silica gel developed with a 20:4:2:1 by volume mixture of ethyl acetate, benzene, ethanol and triethylamine.

Workup

  1. temperaturewas refluxed
  2. customAt the end of this time, the solvent was removed from the residue by evaporation under reduced pressure
  3. customleaving a residue, which
  4. customwas purified by column chromatography through silica gel
  5. washeluted with a 20:4:2:1 by volume mixture of ethyl acetate, benzene, ethanol and triethylamine

Sources & evidence

ORD record
ord-2080dc1dcd4c466293156d8a2a4a013e
Source dataset
uspto-grants-1979_09
Patent number
US04166813

Reaction notes

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