Triglycidylglycerol → 1,2,3-Tris[2-hydroxy-3-(7,7,9,9-tetramethyl-3-octyl-2,4-dioxo-1,3,8-triazaspiro[4.5]dec-8-yl)propoxy]propane

HRID 1758205

Reaction equation

HRID 1758205 reaction equation
[CH3:1][C:2]1([CH3:24])[NH:21][C:20]([CH3:23])([CH3:22])[CH2:19][C:4]2([NH:8][C:7](=[O:9])[N:6]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:5]2=[O:18])[CH2:3]1.[O:25]1[CH2:42][CH:26]1[CH2:27][O:28][CH2:29][CH:30]([CH2:36][O:37][CH2:38][CH:39]1[O:41][CH2:40]1)[O:31][CH2:32][CH:33]1[O:35][CH2:34]1>C(O)CCCCCCC>[OH:25][CH:26]([CH2:42][N:21]1[C:20]([CH3:23])([CH3:22])[CH2:19][C:4]2([NH:8][C:7](=[O:9])[N:6]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:5]2=[O:18])[CH2:3][C:2]1([CH3:1])[CH3:24])[CH2:27][O:28][CH2:29][CH:30]([O:31][CH2:32][CH:33]([OH:35])[CH2:34][N:21]1[C:20]([CH3:23])([CH3:22])[CH2:19][C:4]2([NH:8][C:7](=[O:9])[N:6]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:5]2=[O:18])[CH2:3][C:2]1([CH3:1])[CH3:24])[CH2:36][O:37][CH2:38][CH:39]([OH:41])[CH2:40][N:21]1[C:20]([CH3:23])([CH3:22])[CH2:19][C:4]2([NH:8][C:7](=[O:9])[N:6]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:5]2=[O:18])[CH2:3][C:2]1([CH3:1])[CH3:24]

Participants

4

Reactant 2

HCID 25795TriglycidylglycerolHCID 112677117,7,9,9-Tetramethyl-3-octyl-1,3,8-triazaspiro[4.5]decane-2,4-dione

Product 1

HCID 205105851,2,3-Tris[2-hydroxy-3-(7,7,9,9-tetramethyl-3-octyl-2,4-dioxo-1,3,8-triazaspiro[4.5]dec-8-yl)propoxy]propane

Reagents, catalysts & solvents 1

HCID 9571-OctanolSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 11.0 g of 7,7,9,9-tetramethyl-3-octyl-1,3,8-triazaspiro[4.5]decane-2,4-dione and 2.6 g of glycerol tris(2,3-epoxypropyl)ether in 10 ml of octanol was heated at 180° C. for 30 hours. After completion of the reaction, the reaction mixture was purified by column chromatography through silica gel eluted with ethyl acetate, giving the desired Compound No. 349 in the form of a colourless oil. The compound had an Rf value of 0.54 on thin-layer chromatography on silica gel when developed with a 10:1 by volume mixture of ethyl acetate and triethylamine.

Workup

  1. customAfter completion of the reaction
  2. customthe reaction mixture was purified by column chromatography through silica gel
  3. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-a71dc88bbf9245bdb2dd4e207ba3866f
Source dataset
uspto-grants-1983_02
Patent number
US04371644

Linked notes

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