Dibromomethane → 3,3'-Methylene-bis[5-(3",5"-di-tert.-butyl-4"-hydroxy-phenylethyl)-5-methyl-hydantoin]

HRID 442073Notes

Reaction equation

HRID 442073 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(Br)Br.[OH-:29].[K+].[CH3:31][N:32]([CH3:35])[CH:33]=[O:34]>>[CH2:31]([N:32]1[C:35](=[O:29])[C:18]([CH2:17][CH2:16][C:7]2[CH:6]=[C:5]([C:1]([CH3:3])([CH3:2])[CH3:4])[C:10]([OH:11])=[C:9]([C:12]([CH3:13])([CH3:15])[CH3:14])[CH:8]=2)([CH3:19])[NH:22][C:33]1=[O:34])[N:20]1[C:19](=[O:24])[C:18]([CH3:25])([CH2:17][CH2:16][C:7]2[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]=2)[NH:22][C:21]1=[O:23]

Participants

5

Reactant 4

HCID 3024DibromomethaneHCID 6228DimethylformamideHCID 14797Potassium HydroxideHCID 214162765-(3'5'-Di-tert-butyl-4'-hydroxyphenylethyl)-5-methylhydantoin

Product 1

HCID 227577703,3'-Methylene-bis[5-(3",5"-di-tert.-butyl-4"-hydroxy-phenylethyl)-5-methyl-hydantoin]

Procedure

34.6 g (0.1 mol) of 5-(3',5'-di-tert.-butyl-4'-hydroxyphenylethyl)-5-methyl-hydantoin, 8.7 g (0.05 mol) of methylene bromide and 38 g (0.1 mol) of potassium hydroxide are initially introduced into 100 ml of dimethylformamide and the mixture is kept at 80° C for 16 hours, whilst stirring. After cooling, insoluble matter is filtered off, first 100 ml of toluene and then 100 ml of water are added and the toluene phase is separated off and repeatedly washed with water. Thereafter, 50 ml of toluene are distilled off under reduced pressure and the residual brown solution is left to stand for 24 hours at room temperature. The resulting precipitate is filtered off and recrystallised from acetonitrile.3,3'-methylene-bis[5-(3",5"-di-tert.-butyl-4"-hydroxy-phenylethyl)-5-methyl-hydantoin] of melting point 222° C (stabiliser No. 20) are thus obtained.

Workup

  1. temperatureAfter cooling
  2. filtrationinsoluble matter is filtered off
  3. additionfirst 100 ml of toluene and then 100 ml of water are added
  4. customthe toluene phase is separated off
  5. washrepeatedly washed with water
  6. distillationThereafter, 50 ml of toluene are distilled off under reduced pressure
  7. waitthe residual brown solution is left
  8. waitto stand for 24 hours at room temperature
  9. filtrationThe resulting precipitate is filtered off
  10. customrecrystallised from acetonitrile

Sources & evidence

ORD record
ord-7f74c83de95a4e9aa29ddaf48f229127
Source dataset
uspto-grants-1977_08
Patent number
US04044019

Reaction notes

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