1-Butanol → HCID 20510602, compound

HRID 1758193Notes

Reaction equation

HRID 1758193 reaction equation
C(O)[CH2:2][CH2:3][CH3:4].[OH:6][CH2:7][CH:8]1[CH2:12][O:11][C:10]2([CH2:17][C:16]([CH3:19])([CH3:18])[NH:15][C:14]([CH3:21])([CH3:20])[CH2:13]2)[O:9]1.[O:22]1[CH2:46][CH:23]1[CH2:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]([C:35]2[CH:40]=[CH:39][C:38]([O:41][CH2:42][CH:43]3[O:45][CH2:44]3)=[CH:37][CH:36]=2)([CH3:34])[CH3:33])=[CH:28][CH:27]=1.[C:47]([O:50][CH2:51][CH3:52])(=[O:49])[CH3:48].[CH2:53]([OH:55])C>C(N(CC)CC)C>[OH:45][CH:43]([CH2:44][N:15]1[C:14]([CH3:21])([CH3:20])[CH2:13][C:47]2([O:49][CH:52]([CH2:53][OH:55])[CH2:51][O:50]2)[CH2:48][C:3]1([CH3:2])[CH3:4])[CH2:42][O:41][C:38]1[CH:39]=[CH:40][C:35]([C:32]([C:29]2[CH:30]=[CH:31][C:26]([O:25][CH2:24][CH:23]([OH:22])[CH2:46][N:15]3[C:14]([CH3:21])([CH3:20])[CH2:13][C:10]4([O:9][CH:8]([CH2:7][OH:6])[CH2:12][O:11]4)[CH2:17][C:16]3([CH3:19])[CH3:18])=[CH:27][CH:28]=2)([CH3:34])[CH3:33])=[CH:36][CH:37]=1

Participants

7

Reactant 5

HCID 2631-ButanolHCID 702EthanolHCID 2286Bisphenol A diglycidyl etherHCID 8857Ethyl AcetateHCID 50162607,7,9,9-TETRAMETHYL-1,4-DIOXA-8-AZASPIRO[4.5]DECANE-2-METHANOL

Product 1

HCID 20510602HCID 20510602, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To 80 ml of n-butanol were added 10.0 g of 2-hydroxymethyl-7,7,9,9-tetramethyl-1,4-dioxa-8-azaspiro[4.5]decane and 6.2 g of 2,2-bis[p-(2,3-epoxypropoxy)phenyl]propane and the mixture was refluxed for 3 days. After completion of the reaction, the solvent was removed from the reaction mixture by evaporation under reduced pressure and ethyl acetate was added to the residue. The ethyl acetate solution was washed with water and dried over anhydrous magnesium sulphate. The residue obtained by removing the solvent, by evaporation under reduced pressure, from the ethyl acetate solution was purified by column chromatography through silica gel eluted with a 20:1:1 by volume mixture of ethyl acetate, ethanol and triethylamine. The desired Compound No. 161 was obtained in the form of a vitreous solid having an Rf value of 0.45 on thin-layer chromatography on silica gel developed with a 20:1:1 by volume mixture of ethyl acetate, ethanol and triethylamine.

Workup

  1. temperaturethe mixture was refluxed for 3 days
  2. customAfter completion of the reaction
  3. customthe solvent was removed from the reaction mixture by evaporation under reduced pressure and ethyl acetate
  4. additionwas added to the residue
  5. washThe ethyl acetate solution was washed with water
  6. dry with materialdried over anhydrous magnesium sulphate
  7. customThe residue obtained
  8. customby removing the solvent
  9. customby evaporation under reduced pressure
  10. customfrom the ethyl acetate solution was purified by column chromatography through silica gel
  11. washeluted with a 20:1:1 by volume mixture of ethyl acetate, ethanol and triethylamine
  12. custom161 was obtained in the form of a vitreous solid

Sources & evidence

ORD record
ord-57a8f25bbb954a10aad3ede7f118afe5
Source dataset
uspto-grants-1983_02
Patent number
US04371644

Reaction notes

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