Water → 3,3'-Hexamethylene-bis [5(3",5"-di-tert-butyl-4"-hydroxyphenylethyl)-5-methylhydantoin]

HRID 442074Notes

Reaction equation

HRID 442074 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH2:16][CH2:17][C:18]2([CH3:25])[NH:22][C:21](=[O:23])[NH:20][C:19]2=[O:24])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].[C:26](=[O:29])([O-])[O-].[K+].[K+].Cl[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]Cl.[OH2:40]>CN(C)C=O>[C:12]([C:9]1[CH:8]=[C:7]([CH2:16][CH2:17][C:18]2([CH3:25])[NH:22][C:21](=[O:23])[N:20]([CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][N:20]3[C:19](=[O:40])[C:18]([CH3:25])([CH2:17][CH2:16][C:7]4[CH:6]=[C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[C:10]([OH:11])=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH:8]=4)[NH:22][C:26]3=[O:29])[C:19]2=[O:24])[CH:6]=[C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[C:10]=1[OH:11])([CH3:15])([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 165511,6-DichlorohexaneHCID 214162765-(3'5'-Di-tert-butyl-4'-hydroxyphenylethyl)-5-methylhydantoin

Product 1

HCID 227577683,3'-Hexamethylene-bis [5(3",5"-di-tert-butyl-4"-hydroxyphenylethyl)-5-methylhydantoin]

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6.95 g (0.02 mol) of 5-(3'5'-di-tert.-butyl-4'-hydroxy-phenylethyl)-5-methylhydantoin, 1.4 g (0.01 mol) of potassium carbonate and 1.55 g (0.01 mol) of 1,6-dichlorohexane in 30 ml of dimethylformamide are stirred for 20 hours at 100° C under nitrogen. After cooling, the mixture is added slowly to 120 ml of water with stirring. The precipitated solid is removed by filtration, dried and dissolved in 40 ml of ethanol and decolorized with charcoal. The ethanol solution is filtered and the filtrate added to 400 ml of water with stirring to yield a thick, white suspension which is then filtered. 3,3'-Hexamethylene-bis [5(3",5"-di-tert.-butyl-4"-hydroxyphenylethyl)-5-methylhydantoin] is thus obtained as a white solid of melting point 100°-112° C. (stabiliser No. 22).

Workup

  1. temperatureAfter cooling
  2. customThe precipitated solid is removed by filtration
  3. customdried
  4. dissolutiondissolved in 40 ml of ethanol
  5. filtrationThe ethanol solution is filtered
  6. additionthe filtrate added to 400 ml of water
  7. stirringwith stirring
  8. customto yield a thick, white suspension which
  9. filtrationis then filtered

Sources & evidence

ORD record
ord-3e077cf141164a4e911eea9fbeaa2ab4
Source dataset
uspto-grants-1977_08
Patent number
US04044019

Reaction notes

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