Acetic Acid → 5-(3',5'-Di-tert.-butyl-4'-hydroxy-phenylethyl)-5-methyl-3-ethoxycarbonylethyl-hydantoin

HRID 1578825Notes

Reaction equation

HRID 1578825 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].[CH2:26]([O:28][C:29](=[O:32])[CH:30]=[CH2:31])[CH3:27].[OH-].C([N+](C)(C)C)C1C=CC=CC=1.C(O)(=O)C>C(O)C.CO.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]([CH2:31][CH2:30][C:29]([O:28][CH2:26][CH3:27])=[O:32])[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

8

Reactant 4

HCID 176Acetic AcidHCID 8821Ethyl AcrylateHCID 66854Benzyltrimethylammonium hydroxideHCID 214162765-(3'5'-Di-tert-butyl-4'-hydroxyphenylethyl)-5-methylhydantoin

Product 1

HCID 214162965-(3',5'-Di-tert.-butyl-4'-hydroxy-phenylethyl)-5-methyl-3-ethoxycarbonylethyl-hydantoinYield 74.6%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

30 g (0.087 mol) of 5-(3',5'-di-tert.-butyl-4'-hydroxyphenylethyl)-5-methyl-hydantoin and 13.1 g (0.131 mol) of acrylic acid ethyl ester are dissolved in 100 ml of ethanol, 2 ml of a 40% strength solution of benzyl-trimethyl-ammonium hydroxide in methanol are added and the mixture is heated under reflux for 12 hours, whilst stirring. Thereafter it is neutralised with glacial acetic acid, diluted with 50 ml of water and cooled whilst stirring. The precipitate formed is filtered off, washed with 50% strength ethanol and recrystallised from 70% strength alcohol. 29 g of 5-(3',5'-di-tert.-butyl-4'-hydroxy-phenylethyl)-5-methyl-3-ethoxycarbonylethyl-hydantoin of melting point 100°C are thus obtained. (Stabiliser No. 9).

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 12 hours
  3. temperaturecooled
  4. stirringwhilst stirring
  5. customThe precipitate formed
  6. filtrationis filtered off
  7. washwashed with 50% strength ethanol
  8. customrecrystallised from 70% strength alcohol

Sources & evidence

ORD record
ord-0e2a991b5c314de7a05105e34b685d81
Source dataset
uspto-grants-1976_02
Patent number
US03939175

Reaction notes

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