Water → Tocol

HRID 1165093

Reaktionsgleichung

Reaktionsgleichung von HRID 1165093
[CH3:1][C:2]([CH2:6][CH2:7][CH2:8][CH:9]([CH3:21])[CH2:10][CH2:11][CH2:12][CH:13]([CH3:20])[CH2:14][CH2:15][CH2:16][CH:17]([CH3:19])[CH3:18])=[CH:3][CH2:4]O.[OH2:22].[CH3:23][CH2:24][CH2:25][CH2:26]CC.C([O:32][CH2:33][CH3:34])(=O)C>C(OCCCC)(=O)C.[Cl-].[Zn+2].[Cl-]>[CH3:1][C:2]1([CH2:6][CH2:7][CH2:8][CH:9]([CH3:21])[CH2:10][CH2:11][CH2:12][CH:13]([CH3:20])[CH2:14][CH2:15][CH2:16][CH:17]([CH3:19])[CH3:18])[CH2:3][CH2:4][C:26]2[C:25](=[CH:24][CH:23]=[C:33]([OH:32])[CH:34]=2)[O:22]1

Komponenten

6

Edukt 3

HCID 962WaterHCID 1453863,7,11,15-Tetramethylhexadec-2-en-1-olHCID 21226206Ethyl acetate hexane

Produkt 1

HCID 9865117TocolAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3007855ZincchlorideKatalysatorHCID 31272Butyl AcetateLösungsmittel2×

Versuchsvorschrift

To 1.10 g (10.0 mmole) of 1,4-hydroquinone and 409 mg (3.00 mmole) of zinc chloride in 5 ml of butyl acetate there was dropwise added, under nitrogen atmosphere, 1.48 g (5.00 mmole) of 3,7,11,15-tetramethyl-2-hexadecen-1-ol in 5 ml of butyl acetate over one hour while refluxing under heating. After the completion of the dropwise addition, the reaction solution was refluxed under heating for additional 30 minutes, followed by allowing the reaction solution to cool, pouring it into water (100 ml) and extracting it twice with ether (100 ml×1; 50 ml×1). The combined extract was successively washed with 150 ml of 5% (w/v) aqueous sodium hydroxide solution (one time), 150 ml of water (one time) and 150 ml of saturated aqueous solution of sodium chloride (one time), followed by drying over anhydrous magnesium sulfate, distilling off the solvent and subjecting the residue to silica gel column chromatography. Thus, 770 mg (2.0 mmole) of the title compound (2) was recovered from the eluted fractions (eluent:hexane-ethyl acetate (10:1). Yield:40%.

Aufarbeitung

  1. temperatureunder heating
  2. additionAfter the completion of the dropwise addition
  3. temperaturethe reaction solution was refluxed
  4. temperatureunder heating for additional 30 minutes
  5. temperatureto cool
  6. extractionextracting it twice with ether (100 ml×1; 50 ml×1)
  7. extractionThe combined extract
  8. washwas successively washed with 150 ml of 5% (w/v) aqueous sodium hydroxide solution (one time), 150 ml of water (one time) and 150 ml of saturated aqueous solution of sodium chloride (one time)
  9. dry with materialby drying over anhydrous magnesium sulfate
  10. distillationdistilling off the solvent

Quellen und Nachweise

ORD-Eintrag
ord-9ce534e93fb649359a9ff39b4498272b
Quelldatensatz
uspto-grants-1990_03
Patentnummer
US04906669

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