Hydrogen Bromide → DL-alpha-Tocopherol

HRID 376506

Reaktionsgleichung

Reaktionsgleichung von HRID 376506
[CH3:1][C:2]1[C:8]([CH3:9])=[C:7]([OH:10])[C:6]([CH3:11])=[CH:5][C:3]=1O.C(=O)(OCC)OCC.Br.[CH3:21][CH:22]([CH2:24][CH2:25][CH2:26][CH:27]([CH2:29][CH2:30][CH2:31][CH:32]([CH2:34][CH2:35][CH2:36][C:37]([OH:41])([CH:39]=[CH2:40])[CH3:38])[CH3:33])[CH3:28])[CH3:23]>[Br-].[Zn+2].[Br-]>[CH3:9][C:8]1[C:2]([CH3:1])=[C:3]2[C:5]([CH2:40][CH2:39][C:37]([CH2:36][CH2:35][CH2:34][CH:32]([CH2:31][CH2:30][CH2:29][CH:27]([CH2:26][CH2:25][CH2:24][CH:22]([CH3:21])[CH3:23])[CH3:28])[CH3:33])([CH3:38])[O:41]2)=[C:6]([CH3:11])[C:7]=1[OH:10]

Komponenten

6

Edukt 4

HCID 260Hydrogen BromideHCID 7766Diethyl CarbonateHCID 10453IsophytolHCID 12785Trimethylhydroquinone

Produkt 1

HCID 2116DL-alpha-TocopherolAusbeute 101,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 10421208Zinc bromideKatalysator

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a mixture consisting of 23.3 g (0.153 mol) of 2,3,5-trimethylhydroquinone, 23.2 g (0.153 mol) of zinc bromide, 52.9 ml of diethyl carbonate and 4.3 g of 47% hydrobromic acid, was added dropwise, under stirring at 50±5° C. over one hour, 46.2 g (0.153 ml) of isophytol (purity: 98.1%). Further, the resulting mixture was stirred for one hour at the same temperature. The reaction liquid was washed several times with 50 ml of water, followed by concentrating under a reduced pressure, whereby 66.7 g of the title compound was obtained as a brown oil (yield: 99.1 %, GLC purity: 98.0%).

Aufarbeitung

  1. additionwas added dropwise
  2. stirringFurther, the resulting mixture was stirred for one hour at the same temperature
  3. customThe reaction liquid
  4. washwas washed several times with 50 ml of water
  5. concentrationby concentrating under a reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-6e997ba4f955466e8f03b9847f05127f
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06020505

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