Stearyl Alcohol → Octadecyl DI-tert-butyl-4-hydroxyhydrocinnamate

HRID 1090556Notes

Reaction equation

HRID 1090556 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH2:16][CH2:17][C:18]([O:20][CH3:21])=[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](O)[CH2:23][CH2:24][CH2:25][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]C.C([Sn]=O)CCC.[Si]([O-])([O-])([O-])[O-].[Mg+2].[Mg+2]>>[C:1]([C:5]1[CH:6]=[C:7]([CH2:16][CH2:17][C:18]([O:20][CH2:21][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH3:22])=[O:19])[CH:8]=[C:9]([C:12]([CH3:13])([CH3:14])[CH3:15])[C:10]=1[OH:11])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 4

HCID 8221Stearyl AlcoholHCID 62603Methyl di-t-butyl hydroxyhydrocinnamateHCID 66225Magnesium orthosilicateHCID 6328285Stannane, butyloxo-

Product 1

HCID 16386Octadecyl DI-tert-butyl-4-hydroxyhydrocinnamate

Conditions

Temperature
60 °C

Procedure

Octadecyl 3-(3,5-di-tertbutyl-4-hydroxyphenyl)-propionate was prepared from 124.8 g (0.427 mole) of methyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, 88.8 g (0.328 mole) of octadecyl alcohol and 0.13 g (0.0007 mole) of monobutyltin oxide. To the solution (214 g) of it was added 35 g of synthetic magnesium silicate (manufactured by Mizusawa Chemical Co.), and the solution was stirred at 60° C. for 0.5 hour. The organic layer wa separated by filtration. The residual tin content was 3 ppm (removal rate: 99.2%).

Workup

  1. customThe organic layer wa separated by filtration
  2. custom3 ppm (removal rate: 99.2%)

Sources & evidence

ORD record
ord-aaa2b528f5324cde8f8e3962438dfadb
Source dataset
uspto-grants-1992_01
Patent number
US05081280

Reaction notes

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