Isooctan-1-ol → Octyl beta-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate

HRID 491278Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 491278
[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][CH:27](C)[CH3:28]>CC(C)[O-].[Al+3].CC(C)[O-].CC(C)[O-]>[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][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[O:11])([CH3:3])([CH3:4])[CH3:2]

Komponenten

4

Edukt 2

HCID 15450Isooctan-1-olHCID 62603Methyl di-t-butyl hydroxyhydrocinnamate

Produkt 1

HCID 9908458Octyl beta-(3,5-di-tert-butyl-4-hydroxyphenyl)propionateAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 11143Aluminum isopropoxideKatalysator

Versuchsvorschrift

Methyl 3,5-di-tert-butyl-4-hydroxyhydrocinnamate (256 g, 0.88 mole) and isooctanol (133 g, 0.91 mole) are added to a laboratory reactor equipped with the necessary auxiliary equipment. The mixture is heated to 85 C under a vacuum of 30 mmHg. After fifteen minutes, the vacuum is released and aluminum isopropoxide (1.77 g, 0.0087 mole, Rhone-Poulenc, Manalox 130) is added. The reaction mass is heated to 130 C while under a vacuum of 75 mmHg. After two hours, the reaction mass is heated to 165 C while under a vacuum of 30 mmHg for one hour. The excess isooctanol is removed by vacuum distillation at 165 C. The title compound (331 g, 97% yield) is obtained as a light yellow oil whose assay is 97% as judged by calibrated gas chromatography.

Aufarbeitung

  1. customequipped with the necessary auxiliary equipment
  2. temperatureThe mixture is heated to 85 C under a vacuum of 30 mmHg
  3. waitAfter fifteen minutes
  4. temperatureThe reaction mass is heated to 130 C while under a vacuum of 75 mmHg
  5. temperaturethe reaction mass is heated to 165 C while under a vacuum of 30 mmHg for one hour
  6. customThe excess isooctanol is removed by vacuum distillation at 165 C

Quellen und Nachweise

ORD-Eintrag
ord-dfe2b5ee4f4843c1af78a0423c7fd8c6
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07531487B2

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