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

HRID 974356Notes

Reaction equation

HRID 974356 reaction equation
[CH:1]([CH:13]1[CH2:18][C:17](=[O:19])[O:16][C:14]1=O)=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11].[C:20]([C:24]1[CH:25]=[C:26]([CH2:35][CH2:36][C:37]([NH:39][NH2:40])=[O:38])[CH:27]=[C:28]([C:31]([CH3:34])([CH3:33])[CH3:32])[C:29]=1[OH:30])([CH3:23])([CH3:22])[CH3:21].C1(C)C=CC=CC=1>O>[C:31]([C:28]1[CH:27]=[C:26]([CH2:35][CH2:36][C:37]([NH:39][N:40]2[C:17](=[O:19])[CH2:18][CH:13]([CH:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]([CH3:11])[CH3:12])[C:14]2=[O:16])=[O:38])[CH:25]=[C:24]([C:20]([CH3:21])([CH3:22])[CH3:23])[C:29]=1[OH:30])([CH3:32])([CH3:33])[CH3:34]

Participants

5

Reactant 3

HCID 1140TolueneHCID 648653,5-Di-tert-butyl-4-hydroxyhydrocinnamic acid hydrazideHCID 54070354Isododecenylsuccinic Anhydride

Product 1

HCID 86745247N-[3-(3,5-di-t-butyl-4-hydroxyphenyl)propanamido]-2-isododecenylsuccinimideYield 102.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-isododecenylsuccinic anhydride (31.2 g, 111 mmol), 3-(3,5-di-t-butyl-4-hydroxy-phenyl)propanoic acid hydrazide (32.6 g, 111 mmol) and 60 ml of toluene was refluxed for 90 minutes under a nitrogen atmosphere with the azeotropic removal of water (Dean-Stark assembly). The bulk of the solvent was distilled off followed by vacuum stripping of the hot (135° C.) melt for 25 minutes to remove last traces of solvent. After cooling to room temperature, the vacuum was removed. Additional cooling in an acetone/dry ice bath allowed for easy removal of the thermally fractured solid from the vessel. 61.7 g of an amber solid was obtained having a melting range of 62°-68° C.

Workup

  1. distillationThe bulk of the solvent was distilled off
  2. customto remove last traces of solvent
  3. customthe vacuum was removed
  4. temperatureAdditional cooling in an acetone/dry ice bath
  5. customallowed for easy removal of the thermally fractured solid from the vessel

Sources & evidence

ORD record
ord-5824a42b6e6b43dbb446b4a6c51fa731
Source dataset
uspto-grants-1991_11
Patent number
US05068356

Reaction notes

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