Ethyl Acetate → Bis{4-[2-hydroxy-3-(7,7,9,9-tetramethyl-2,4-dioxo-1,3,8-triazaspiro[4.5]dec-3-yl)propoxy]phenyl}methane

HRID 972028Notes

Reaction equation

HRID 972028 reaction equation
[CH3:1][C:2]1([CH3:16])[NH:13][C:12]([CH3:15])([CH3:14])[CH2:11][C:4]2([NH:8][C:7](=[O:9])[NH:6][C:5]2=[O:10])[CH2:3]1.O1[CH2:39][CH:18]1[CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH:36]3[O:38][CH2:37]3)=[CH:30][CH:29]=2)=[CH:23][CH:22]=1.[OH-:40].[K+].C([O:45][CH2:46][CH3:47])(=O)C>CO.C(N(CC)CC)C.C(O)C>[OH:40][CH:18]([CH2:39][N:8]1[C:46](=[O:45])[C:47]2([CH2:1][C:2]([CH3:16])([CH3:3])[NH:13][C:12]([CH3:14])([CH3:11])[CH2:15]2)[NH:6][C:7]1=[O:9])[CH2:19][O:20][C:21]1[CH:22]=[CH:23][C:24]([CH2:27][C:28]2[CH:29]=[CH:30][C:31]([O:34][CH2:35][CH:36]([OH:38])[CH2:37][N:6]3[C:5](=[O:10])[C:4]4([CH2:3][C:2]([CH3:16])([CH3:1])[NH:13][C:12]([CH3:15])([CH3:14])[CH2:11]4)[NH:8][C:7]3=[O:9])=[CH:32][CH:33]=2)=[CH:25][CH:26]=1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 14797Potassium HydroxideHCID 91511Bisphenol F diglycidyl etherHCID 12680667,7,9,9-Tetramethyl-1,3,8-triazaspiro[4.5]decane-2,4-dione

Product 1

HCID 20396782Bis{4-[2-hydroxy-3-(7,7,9,9-tetramethyl-2,4-dioxo-1,3,8-triazaspiro[4.5]dec-3-yl)propoxy]phenyl}methane

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 12 g of 7,7,9,9-tetramethyl-1,3,8-triazaspiro[4.5]decane-2,4-dione, 7 g of bis[p-(2,3-epoxypropoxy)phenyl]methane and 0.1 g (a catalytic amount) of potassium hydroxide was refluxed for 7 hours in 50 ml of methanol. After completion of the reaction, the methanol was evaporated under reduced pressure from the reaction mixture and the residue was dissolved in chloroform. The solution was then washed successively with a 5% w/w aqueous solution of potassium hydroxide and water and dried over anhydrous magnesium sulphate. The solvent was evaporated off under reduced pressure, leaving a residue which was recrystallised from a mixture of benzene and methanol. The desired Compound No. 179 was obtained in the form of white crystals, melting point 113°-118° C. The compound had an Rf value of 0.42 on thin-layer chromatography on silica gel using a 8:1:1 by volume mixture of ethyl acetate, ethanol and triethylamine as developing solvent.

Workup

  1. customAfter completion of the reaction
  2. customthe methanol was evaporated under reduced pressure from the reaction mixture
  3. dissolutionthe residue was dissolved in chloroform
  4. washThe solution was then washed successively with a 5% w/w aqueous solution of potassium hydroxide and water
  5. dry with materialdried over anhydrous magnesium sulphate
  6. customThe solvent was evaporated off under reduced pressure
  7. customleaving a residue which
  8. customwas recrystallised from a mixture of benzene and methanol
  9. custom179 was obtained in the form of white crystals, melting point 113°-118° C

Sources & evidence

ORD record
ord-4c05aa5091bd4cab89c7413b43611674
Source dataset
uspto-grants-1979_07
Patent number
US04162246

Reaction notes

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