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

HRID 1596806Notes

Reaction equation

HRID 1596806 reaction equation
[CH2:1]([OH:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[C:20]([C:24]1[CH:25]=[C:26]([CH:33]=[C:34]([C:37]([CH3:40])([CH3:39])[CH3:38])[C:35]=1[OH:36])[CH2:27][CH2:28][C:29](OC)=[O:30])([CH3:23])([CH3:22])[CH3:21]>>[C:37]([C:34]1[CH:33]=[C:26]([CH:25]=[C:24]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:35]=1[OH:36])[CH2:27][CH2:28][C:29]([O:19][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:30])([CH3:39])([CH3:40])[CH3:38]

Participants

3

Reactant 2

HCID 8221Stearyl Alcohol2×HCID 62603Methyl di-t-butyl hydroxyhydrocinnamate2×

Product 1

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

Procedure

The general procedure of Example 1 is repeated, but using 382.9 g (1.416 mole) of octadecyl alcohol and 471.3 g (1.612 mole) of methyl 3,5-di-tert-butyl-4-hydroxyhydrocinnamate and employing 2 ounces (30.1 g) of PROPAK® and 2.5 ounces (69.4 g) of TiS catalyst. The system is brought to reflux at a pressure of 6-8 mm Hg and a temperature of between 190 and 202° C. After 2.5 hours, analysis of the contents of the reaction flask using Gas Chromatography shows a mixture of 51.7 wt % of the title compound, 26.2 wt % of methyl 3,5-di-tert-butyl-4-hydroxyhydrocinnamate and 20.8 wt % octadecyl alcohol.

Workup

  1. temperatureto reflux at a pressure of 6-8 mm Hg
  2. customa temperature of between 190 and 202° C

Sources & evidence

ORD record
ord-4de0c564f8d74d2594e34c9682566c00
Source dataset
uspto-grants-2001_09
Patent number
US06291703B1

Reaction notes

Loading…