Hydrochloric Acid → 3,3'-Hexamethylene-bis[5-(3",5"-di-tert-butyl-4"-hydroxyphenylethyl)-5-methyl-1-n-hexylhydantoin]

HRID 442075Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 442075
[C:1]([C:5]1[CH:6]=[C:7]([CH2:16][CH2:17][C:18]2([CH3:56])[NH:22][C:21](=[O:23])[N:20]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][N:30]3[C:34](=[O:35])[C:33]([CH3:53])([CH2:36][CH2:37][C:38]4[CH:43]=[C:42]([C:44]([CH3:47])([CH3:46])[CH3:45])[C:41]([OH:48])=[C:40]([C:49]([CH3:52])([CH3:51])[CH3:50])[CH:39]=4)[NH:32][C:31]3=[O:54])[C:19]2=[O:55])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH3:65].Cl>CN(C)C=O.O>[C:44]([C:42]1[CH:43]=[C:38]([CH2:37][CH2:36][C:33]2([CH3:53])[N:32]([CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH3:65])[C:31](=[O:54])[N:30]([CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][N:20]3[C:19](=[O:55])[C:18]([CH3:56])([CH2:17][CH2:16][C:7]4[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]([OH:11])=[C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[CH:6]=4)[N:22]([CH2:2][CH2:1][CH2:5][CH2:10][CH2:9][CH3:8])[C:21]3=[O:23])[C:34]2=[O:35])[CH:39]=[C:40]([C:49]([CH3:52])([CH3:51])[CH3:50])[C:41]=1[OH:48])([CH3:47])([CH3:46])[CH3:45]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 81011-BromohexaneHCID 24758Sodium hydrideHCID 227577683,3'-Hexamethylene-bis [5(3",5"-di-tert-butyl-4"-hydroxyphenylethyl)-5-methylhydantoin]

Produkt 1

HCID 214163023,3'-Hexamethylene-bis[5-(3",5"-di-tert-butyl-4"-hydroxyphenylethyl)-5-methyl-1-n-hexylhydantoin]

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

7.75 g (0.01 mol) of 3,3'-hexamethylene-bis-[5-(3",5"-di-tert-butyl-4"-hydroxyphenylethyl)-5-methylhydantoin] is added portionwise with stirring to a slurry of 1.92 g (0.04 mol) of a 50% dispersion of sodium hydride in mineral oil in 100 g of dry dimethylformamide. The temperature of the reaction mixture is maintained at 50°-55° C until gas evolution ceases. 3.3 g (0.02 mol) of 1-bromohexane is then added dropwise over a period of 15-30 minutes. The temperature of the mixture is maintained between 60°-80° C until the reaction is complete. The reaction mixture is then poured into water and neutralized with dilute hydrochloric acid. The mixture is then extracted with chloroform. The chloroform phase is dried and completely concentrated under reduced pressure to yield as the residue the desired 3,3'-hexamethylene-bis[5-(3",5"-di-tert-butyl-4"-hydroxyphenylethyl)-5-methyl-1-n-hexylhydantoin].

Aufarbeitung

  1. temperatureThe temperature of the reaction mixture is maintained at 50°-55° C until gas evolution ceases
  2. temperatureThe temperature of the mixture is maintained between 60°-80° C until the reaction
  3. extractionThe mixture is then extracted with chloroform
  4. dry with materialThe chloroform phase is dried
  5. concentrationcompletely concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-bd78779821904f0bbb6d2658dd369735
Quelldatensatz
uspto-grants-1977_08
Patentnummer
US04044019

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