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

HRID 974358Notes

Reaction equation

HRID 974358 reaction equation
[CH2:1]([CH:13]1[CH2:18][C:17](=[O:19])[O:16][C:14]1=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[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]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][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 98107Dodecylsuccinic anhydride

Product 1

HCID 15044331N-[3-(3,5-di-t-butyl-4-hydroxyphenyl)propanamido]-2-dodecylsuccinimide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-dodecylsuccinic anhydride (42.17 g, 147.4 mmol), 3-(3,5-di-t-butyl-4-hydroxyphenyl)propanoic acid hydrazide (43.31 g, 147.4 mmol) and 70 ml of toluene was refluxed for one hour 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 (160° C.) melt for about 10 minutes. The resulting yellow liquid was then cooled under vacuum to about 120° C. The vacuum was released and the melt was quickly poured into a container. Upon cooling, the liquid became a clear yellow glass. The product was recrystallized from acetone/water at ice bath temperatures to afford, after drying, a nearly quantitative recovery of the product as a white powder having a melting range of 55°-60° C.

Workup

  1. distillationThe bulk of the solvent was distilled off
  2. additionthe melt was quickly poured into a container
  3. temperatureUpon cooling
  4. customThe product was recrystallized from acetone/water at ice bath temperatures
  5. customto afford
  6. customafter drying

Sources & evidence

ORD record
ord-1de2618db0f7495faa55128798ac3afc
Source dataset
uspto-grants-1991_11
Patent number
US05068356

Reaction notes

Loading…