O-Xylene → 2-Stearamidoethyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate

HRID 1659899Notes

Reaction equation

HRID 1659899 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH2:16][CH2:17][C:18]([OH:20])=[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].O[CH2:22][CH2:23][NH:24][C:25](=[O:43])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42].C1(C)C(C)=CC=CC=1>CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-].[Ti+4].O>[C:1]([C:5]1[CH:6]=[C:7]([CH2:16][CH2:17][C:18]([O:20][CH2:22][CH2:23][NH:24][C:25](=[O:43])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])=[O:19])[CH:8]=[C:9]([C:12]([CH3:13])([CH3:14])[CH3:15])[C:10]=1[OH:11])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 7237O-XyleneHCID 27902N-StearoylethanolamineHCID 883893-(3',5'-Di-tert-butyl-4'-hydroxyphenyl)propionic acid

Product 1

HCID 205584912-Stearamidoethyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate

Reagents, catalysts & solvents 2

HCID 21801Titanium tetrabutoxideCatalystHCID 962WaterSolvent

Procedure

A mixture of 30.6 g (0.11 mole) 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid, 32.6 g (0.1 mole) N-(2-hydroxyethyl)stearamide, 0.8 g Tyzor TBT, and 100 ml xylene was refluxed for six hours. The water (1.8 ml) was trapped in a Stark & Dean trap. The solution was filtered through Microcel (trademark, synthetic calcium silicate) and the solvent was removed by vacuum stripping. The title compound (51 g) was recrystallized from acrylonitrile. It melted at 52°-55° C.

Workup

  1. temperaturewas refluxed for six hours
  2. filtrationThe solution was filtered through Microcel (trademark, synthetic calcium silicate)
  3. customthe solvent was removed by vacuum stripping
  4. customThe title compound (51 g) was recrystallized from acrylonitrile

Sources & evidence

ORD record
ord-17febe92b6be438884d353ab4e1d39ed
Source dataset
uspto-grants-1981_12
Patent number
US04305868

Reaction notes

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