Hydrochloric Acid → alpha-Tocopherol

HRID 376502

Reaktionsgleichung

Reaktionsgleichung von HRID 376502
[CH3:1][C:2]1[C:8]([CH3:9])=[C:7]([OH:10])[C:6]([CH3:11])=[CH:5][C:3]=1O.Cl.[CH3:13][CH:14]([CH2:16][CH2:17][CH2:18][CH:19]([CH2:21][CH2:22][CH2:23][CH:24]([CH2:26][CH2:27][CH2:28][C:29]([OH:33])([CH:31]=[CH2:32])[CH3:30])[CH3:25])[CH3:20])[CH3:15]>[Cl-].[Zn+2].[Cl-].C(=O)(OCC)OCC>[CH3:9][C:8]1[C:7]([OH:10])=[C:6]([CH3:11])[C:5]2[CH2:32][CH2:31][C@:29]([CH2:28][CH2:27][CH2:26][C@@H:24]([CH2:23][CH2:22][CH2:21][C@@H:19]([CH2:18][CH2:17][CH2:16][CH:14]([CH3:13])[CH3:15])[CH3:20])[CH3:25])([CH3:30])[O:33][C:3]=2[C:2]=1[CH3:1]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 10453IsophytolHCID 12785Trimethylhydroquinone

Produkt 1

HCID 14985alpha-TocopherolAusbeute 101,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3007855ZincchlorideKatalysatorHCID 7766Diethyl CarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
35 °C

Versuchsvorschrift

To a mixture consisting of 23.3 g (0.153 mol) of 2,3,5-trimethylhydroquinone, 17.5 g (128 mol) of zinc chloride, 50 ml of diethyl carbonate and 2.5 g of concentrated hydrochloric acid, 46.1 g (0.153 mol) of isophytol (purity: 98.3%) was added dropwise under stirring at 30-40° C. over 3 hours. At the same temperature, the reaction mixture was stirred for an additional 2 hours. After the reaction mixture was washed with 10 ml of water, the solvent was distilled off. Toluene (100 ml) was added to the residue to dissolve the same. The resulting solution was washed successively with water, alkaline water and a saturated aqueous solution of NaCl, dried over magnesium sulfate and then concentrated under reduced pressure, whereby 67.0 g of the title compound was obtained as a brown oil (yield: 98.9%, GLC purity: 97.3%).

Aufarbeitung

  1. additionwas added dropwise
  2. stirringAt the same temperature, the reaction mixture was stirred for an additional 2 hours
  3. washAfter the reaction mixture was washed with 10 ml of water
  4. distillationthe solvent was distilled off
  5. additionToluene (100 ml) was added to the residue
  6. dissolutionto dissolve the same
  7. washThe resulting solution was washed successively with water
  8. dry with materialalkaline water and a saturated aqueous solution of NaCl, dried over magnesium sulfate
  9. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f7cec633ffa9457b8bec56ef82612827
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06020505

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