Reaktion #319580

Reaktionsgleichung

1,2-epoxy-2,6,10,14-tetramethylpentadecane

tetramethylhydroquinone

sodium

hydrochloric acid

butyllithium

→

α-tocopherol

Ausbeute 78.1%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITthe mixture is left
2. 2
   Sonstigeto react for 12 hours
3. 3
   workup.STIRRINGwhile stirring
4. 4
   workup.STIRRINGthe mixture is stirred at 50° C. for 2 hours
5. 5
   EinengenThe mixture is subsequently concentrated at 50° C.
6. 6
   Sonstigethe residue is chromatographed on silica gel with toluene, whereby where

Vorschrift

10 g (66.7 mmol) of tetramethylhydroquinone are dissolved in 100 ml of dry tetrahydrofuran, 4 g (139 mmol) of sodium hydridge (80% in mineral oil) was added thereto at room temperature, 45 ml of butyllithium (1.6 molar in hexane) are subsequently added dropwise and the mixture is stirred for 1 hour. 10 g (44.3 mmol) of 1,2-epoxy-2,6,10,14-tetramethylpentadecane are now added dropwise; the mixture is left to react for 12 hours while stirring. 100 ml of 1N methanolic hydrochloric acid area added and the mixture is stirred at 50° C. for 2 hours. The mixture is subsequently concentrated at 50° C. and the residue is chromatographed on silica gel with toluene, whereby where are obtained 14.9 g (75%) of α-tocopherol.

Quelle