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

HRID 443088

Reaktionsgleichung

Reaktionsgleichung von HRID 443088
[C:1]([C:5]1[CH:6]=[C:7]([CH:14]=[C:15]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:16]=1[OH:17])[CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O: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)CCCC)CCC>>[C:1]([C:5]1[CH:6]=[C:7]([CH:14]=[C:15]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:16]=1[OH:17])[CH2:8][CH2:9][C:10]([O:12][CH2:13][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:11])([CH3:3])([CH3:4])[CH3:2]

Komponenten

4

Edukt 3

HCID 8221Stearyl AlcoholHCID 61221Dibutyltin oxideHCID 62603Methyl di-t-butyl hydroxyhydrocinnamate

Produkt 1

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

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

In a reactor fitted with a heating/cooling bath, stirrer, thermocouple, nitrogen inlet, a reflux condenser with a trap to collect distilled off methanol, and a vacuum connection are added 438.6 g (1.5 moles, a 5% excess) of methyl 3,5-di-tert-butyl-4-hydroxyhydrocinnamate and 386.8 g (1.43 moles) of 1-octadecanol. The mixture is heated to 100° C. under nitrogen with stirring. After drying at 100° C. under vacuum (≤5 mm Hg) for 30 minutes, the mixture is heated to 120° C. under nitrogen and 0.05 g (0.0002 mole) of dibutyltin oxide (Fascat® 4201, Elf-Atochem) is added. The vacuum is lowered to 100 mm Hg and the reaction mixture is heated to 185° C. for one hour. The vacuum is slowly lowered to 2 mm Hg over 1.5 hours and kept at that temperature and pressure for another thirty minutes. The vacuum is broken with nitrogen and the reaction mass is cooled to 100° C. The excess methyl 3,5-di-tert-butyl-4-hydroxyhydrocinnamate is removed using a wiped-film evaporator to give the title compound as a white solid containing 30 ppm Sn. Essentially a quantitative yield (99.8) of the ester product is obtained.

Aufarbeitung

  1. customIn a reactor fitted with a heating/cooling bath, stirrer
  2. customthermocouple, nitrogen inlet, a reflux condenser with a trap to collect
  3. distillationdistilled off methanol
  4. additiona vacuum connection are added 438.6 g (1.5 moles
  5. customAfter drying at 100° C. under vacuum (≤5 mm Hg) for 30 minutes
  6. temperaturethe mixture is heated to 120° C. under nitrogen
  7. temperaturethe reaction mixture is heated to 185° C. for one hour
  8. waitkept at that temperature and pressure for another thirty minutes
  9. temperaturethe reaction mass is cooled to 100° C
  10. customThe excess methyl 3,5-di-tert-butyl-4-hydroxyhydrocinnamate is removed
  11. customa wiped-film evaporator

Quellen und Nachweise

ORD-Eintrag
ord-32a44f796ed6418399a6db67823c8614
Quelldatensatz
uspto-grants-1999_04
Patentnummer
US05892097

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