Toluene → N-[3-(3,5-di-t-butyl-4-hydroxyphenyl)propanamido]-2-hexadecylsuccinimide

HRID 974353Notes

Reaction equation

HRID 974353 reaction equation
[CH2:1]([CH:17]1[CH2:22][C:21](=[O:23])[O:20][C:18]1=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[C:24]([C:28]1[CH:29]=[C:30]([CH2:39][CH2:40][C:41]([NH:43][NH2:44])=[O:42])[CH:31]=[C:32]([C:35]([CH3:38])([CH3:37])[CH3:36])[C:33]=1[OH:34])([CH3:27])([CH3:26])[CH3:25].C1(C)C=CC=CC=1>O>[C:35]([C:32]1[CH:31]=[C:30]([CH2:39][CH2:40][C:41]([NH:43][N:44]2[C:21](=[O:23])[CH2:22][CH:17]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[C:18]2=[O:20])=[O:42])[CH:29]=[C:28]([C:24]([CH3:25])([CH3:26])[CH3:27])[C:33]=1[OH:34])([CH3:36])([CH3:37])[CH3:38]

Participants

5

Reactant 3

HCID 1140TolueneHCID 648653,5-Di-tert-butyl-4-hydroxyhydrocinnamic acid hydrazideHCID 778682,5-Furandione, 3-hexadecyldihydro-

Product 1

HCID 15044324N-[3-(3,5-di-t-butyl-4-hydroxyphenyl)propanamido]-2-hexadecylsuccinimideYield 101.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

2-Hexadecylsuccinic anhydride (10.5 g, 31.3 mmol), 3-(3,5-di-t-butyl-4-hydroxyphenyl)propanoic acid hydrazide (9.2 g, 31.3 mmol) and 10 ml of toluene were combined and refluxed for one hour under a nitrogen atmosphere with the azeotropic removal of water. Solvent was then removed under vacuum as the mixture was warmed to about 130° C. After 20 minutes, the reaction mixture was cooled and the vacuum was removed. The resulting viscous yellow mass was further chilled in an acetone/dry ice bath causing the mass to harden for facile removal from the reaction vessel. About 19 g of a viscous yellow gum was obtained that solidified to a translucent white solid upon standing for several days at room temperature.

Workup

  1. customSolvent was then removed under vacuum as the mixture
  2. temperaturethe reaction mixture was cooled
  3. customthe vacuum was removed
  4. temperatureThe resulting viscous yellow mass was further chilled in an acetone/dry ice bath
  5. customto harden for facile removal from the reaction vessel

Sources & evidence

ORD record
ord-31c848e6eb854198a7060527855872ad
Source dataset
uspto-grants-1991_11
Patent number
US05068356

Reaction notes

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