Isooctan-1-ol → Octyl 3-(3-(2H-benzotriazol-2-yl)-5-tert-butyl-4-hydroxyphenyl)propanoate

HRID 1582839

Reaktionsgleichung

Reaktionsgleichung von HRID 1582839
[N:1]1[N:2]([C:10]2[CH:11]=[C:12]([CH:19]=[C:20]([C:23]([CH3:26])([CH3:25])[CH3:24])[C:21]=2[OH:22])[CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])[N:3]=[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.[CH2:27](O)[CH2:28][CH2:29][CH2:30][CH2:31][CH:32](C)[CH3:33].C([Sn](=O)CCCC)CCC>>[N:1]1[N:2]([C:10]2[CH:11]=[C:12]([CH:19]=[C:20]([C:23]([CH3:26])([CH3:25])[CH3:24])[C:21]=2[OH:22])[CH2:13][CH2:14][C:15]([O:17][CH2:18][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[O:16])[N:3]=[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12

Komponenten

4

Edukt 3

HCID 15450Isooctan-1-olHCID 61221Dibutyltin oxideHCID 934812-(3'-tert-Butyl-2'-hydroxy-5'-(2-methoxycarbonylethyl)phenyl)benzotriazole

Produkt 1

HCID 9868461Octyl 3-(3-(2H-benzotriazol-2-yl)-5-tert-butyl-4-hydroxyphenyl)propanoate

Reaktionsbedingungen

Temperatur
175 °C

Versuchsvorschrift

Methyl 3-(2H-benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamate (353 g, 1 mol), isooctanol (260 g, 2 mol, from Exxon) and dibutyltin oxide (0.5 g, 0.002 mol) are charged to a reaction flask and heated to 175° C. While heating to 175° C., a 300 mm Hg vacuum is applied. After holding at 175° C. for 30 minutes, the excess isooctanol is distilled by slowly reducing the pressure to <5 mm Hg. The desired product is cooled and discharged. The title compound is obtained in a yield of 451 g (100%) as a light yellow oil whose structure is verified by 1Hnmr and mass spectroscopy. The non-distilled product is analyzed by ICP (Inductively Coupled Plasma) for tin and is found to contain 170 ppm of tin.

Aufarbeitung

  1. temperatureWhile heating to 175° C.
  2. distillationthe excess isooctanol is distilled
  3. temperatureThe desired product is cooled

Quellen und Nachweise

ORD-Eintrag
ord-5a243d321e1a4a03b6a0ee57399bedda
Quelldatensatz
uspto-grants-2004_05
Patentnummer
US06740132B2

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