Ethylene Glycol → HCID 20510569, compound

HRID 1758197Notes

Reaction equation

HRID 1758197 reaction equation
[CH2:1]([OH:4])[CH2:2]O.[C:5]([OH:9])([CH3:8])([CH3:7])C.[C:10]([O:23][CH2:24][CH2:25][N:26]1[C:30](=[O:31])[C:29]2([CH2:36][C:35]([CH3:38])([CH3:37])[NH:34][C:33]([CH3:40])([CH3:39])[CH2:32]2)[NH:28][C:27]1=[O:41])(=[O:22])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].O1CC1C[O:45][C:46]1[CH:51]=[CH:50][C:49]([C:52]([C:55]2[CH:60]=[CH:59][C:58]([O:61][CH2:62][CH:63]3[O:65][CH2:64]3)=[CH:57][CH:56]=2)([CH3:54])[CH3:53])=[CH:48][CH:47]=1>CO.C(OCC)(=O)C.C1C=CC=CC=1>[OH:65][CH:63]([CH2:64][N:34]1[C:35]([CH3:38])([CH3:37])[CH2:36][C:29]2([NH:28][C:27](=[O:41])[N:26]([CH2:25][CH2:24][O:23][C:1](=[O:4])[CH2:2][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:30]2=[O:31])[CH2:32][C:33]1([CH3:39])[CH3:40])[CH2:62][O:61][C:58]1[CH:57]=[CH:56][C:55]([C:52]([C:49]2[CH:48]=[CH:47][C:46]([O:45][CH2:7][CH:5]([OH:9])[CH2:8][N:34]3[C:35]([CH3:38])([CH3:37])[CH2:36][C:29]4([NH:28][C:27](=[O:41])[N:26]([CH2:25][CH2:24][O:23][C:10](=[O:22])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:30]4=[O:31])[CH2:32][C:33]3([CH3:40])[CH3:39])=[CH:51][CH:50]=2)([CH3:54])[CH3:53])=[CH:60][CH:59]=1

Participants

8

Reactant 4

HCID 174Ethylene GlycolHCID 2286Bisphenol A diglycidyl etherHCID 6386tert-ButanolHCID 20510563HCID 20510563, compound

Product 1

HCID 20510569HCID 20510569, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolvent2×HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixed solvent consisting of 1.0 g of ethylene glycol and 1.0 g of t-butanol were added 3.9 g of 3-(2-lauroyloxyethyl)-7,7,9,9-tetramethyl-1,3,8-triazaspiro[4.5]decane-2,4-dione and 1.2 g of 2,2-bis[p-(2,3-epoxypropoxy)phenyl]propane; the mixture was heated at 110°-120° C. for 60 hours and then at 160° C. for an additional 1 hour. After completion of the reaction, benzene was added to the reaction mixture, and the benzene solution was washed with water and condensed by evaporation under reduced pressure. The residue was washed with n-hexane and the resulting solid mass was purified by column chromatography using silica gel eluted with a 20:20:1 by volume mixture of benzene, ethyl acetate and methanol. The desired Compound No. 294 was obtained in the form of a white powder and had an Rf value of 0.64 on thin-layer chromatography on silica gel developed with a 10:10:1 by volume mixture of benzene, ethyl acetate and methanol.

Workup

  1. temperaturethe mixture was heated at 110°-120° C. for 60 hours
  2. additionwas added to the reaction mixture
  3. washthe benzene solution was washed with water and condensed by evaporation under reduced pressure
  4. washThe residue was washed with n-hexane
  5. customthe resulting solid mass was purified by column chromatography
  6. washeluted with a 20:20:1 by volume mixture of benzene, ethyl acetate and methanol
  7. custom294 was obtained in the form of a white powder

Sources & evidence

ORD record
ord-daf56cd711b6480f9761d251bdd08ed8
Source dataset
uspto-grants-1983_02
Patent number
US04371644

Reaction notes

Loading…