Acetic Acid → 5-(3',5'-Di-tert-butyl-4'-hydroxyphenylethyl)-5-methyl-1-n-octadecylhydantoin

HRID 442076Notes

Reaction equation

HRID 442076 reaction equation
[C-]#N.[K+].[CH3:4][C:5]([CH2:7][CH2:8][C:9]1[CH:14]=[C:13]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:12]([OH:19])=[C:11]([C:20]([CH3:23])([CH3:22])[CH3:21])[CH:10]=1)=O.[CH2:24]([NH2:42])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41].[O-:43][C:44]#[N:45].[K+].[C:47](O)(=[O:49])C>O.Cl>[C:20]([C:11]1[CH:10]=[C:9]([CH2:8][CH2:7][C:5]2([CH3:4])[N:42]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[C:47](=[O:49])[NH:45][C:44]2=[O:43])[CH:14]=[C:13]([C:15]([CH3:16])([CH3:17])[CH3:18])[C:12]=1[OH:19])([CH3:21])([CH3:23])[CH3:22]

Participants

8

Reactant 5

HCID 176Acetic Acid2×HCID 9032Potassium CyanideHCID 15793OctadecylamineHCID 39609622-Butanone, 4-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-HCID 11378442Potassium cyanate

Product 1

HCID 214162775-(3',5'-Di-tert-butyl-4'-hydroxyphenylethyl)-5-methyl-1-n-octadecylhydantoin

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent4×

Procedure

7.8 g (0.12 mole) of potassium cyanide in 40 ml of water is slowly added to a stirred solution of 27.6 g (0.1 mole) of 3,5-di-tert-butyl-4-hydroxyphenylethyl methyl ketone and 27.0 g (0.1 mol) of n-octadecylamine in 200 ml of glacial acetic acid at 15°-25° C. The mixture is stirred at 20°-25° C for 3.5 hours after addition is complete and then allowed to stand overnight at room temperature. The reaction mixture is then diluted with water and extracted with ether. The ether extract is dried and evaporated to dryness. The crude aminonitrile thus obtained is dissolved in 200 ml of glacial acetic acid containing 10 ml of concentrated hydrochloric acid and reacted with 16.2 g (0.2 mole) of potassium cyanate in 50 ml of water. The reaction mixture is warmed at 35°-50° C for 3 hours, then cooled and poured into water. The solid obtained is removed by filtration and then refluxed with 300 ml of 20% aqueous hydrochloric acid for 30 minutes. The solution is cooled and then desired product, 5-(3',5'-di-tert-butyl-4'-hydroxyphenylethyl)-5-methyl-1-n-octadecylhydantoin, is isolated by filtration, washed, dried and recrystallized.

Workup

  1. additionafter addition
  2. waitto stand overnight at room temperature
  3. extractionextracted with ether
  4. extractionThe ether extract
  5. customis dried
  6. customevaporated to dryness
  7. customThe crude aminonitrile thus obtained
  8. temperatureThe reaction mixture is warmed at 35°-50° C for 3 hours
  9. temperaturecooled
  10. customThe solid obtained
  11. customis removed by filtration
  12. temperaturerefluxed with 300 ml of 20% aqueous hydrochloric acid for 30 minutes
  13. temperatureThe solution is cooled

Sources & evidence

ORD record
ord-a91a0e2582894908ab6e5f4923d36379
Source dataset
uspto-grants-1977_08
Patent number
US04044019

Reaction notes

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