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

HRID 974355Notes

Reaction equation

HRID 974355 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH2:16][CH2:17][C:18]([NH:20][NH2:21])=[O:19])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].[CH2:22]([CH:30]1[CH2:35][C:34](=O)[O:33][C:31]1=[O:32])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].C1(C)C=CC=CC=1>O>[C:12]([C:9]1[CH:8]=[C:7]([CH2:16][CH2:17][C:18]([NH:20][N:21]2[C:34](=[O:33])[CH2:35][CH:30]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[C:31]2=[O:32])=[O:19])[CH:6]=[C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[C:10]=1[OH:11])([CH3:13])([CH3:14])[CH3:15]

Participants

5

Reactant 3

HCID 1140TolueneHCID 648653,5-Di-tert-butyl-4-hydroxyhydrocinnamic acid hydrazideHCID 778692,5-Furandione, dihydro-3-octyl-

Product 1

HCID 15044325N-[3-(3,5-di-t-butyl-4-hydroxyphenyl)propanamido]-2-octylsuccinimide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-(3,5-di-t-butyl-4-hydroxyphenyl)propanoic acid hydrazide (12.1 g, 41.1 mmol), 2-octylsuccinic anhydride (9.0 g, 41.1 mmol) and 20 ml of toluene was refluxed for one hour under a nitrogen atmosphere with the azeotropic removal of water (Dean-Stark assembly). The solvent was removed under vacuum while heating the reaction mass. 18.7 g of a very viscous, clear yellow liquid was obtained.

Workup

  1. customThe solvent was removed under vacuum
  2. temperaturewhile heating the reaction mass
  3. custom18.7 g of a very viscous, clear yellow liquid was obtained

Sources & evidence

ORD record
ord-ab3a76dd6a5f497d8b51714bca0ecc08
Source dataset
uspto-grants-1991_11
Patent number
US05068356

Reaction notes

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