Reaktion #318450

Reaktionsgleichung

hydrochloric acid

sodium hydride

benzyl alcohol

1,2-epoxy-3-(12-cyclohexyldodecyloxy)propane

→

captioned compound

Ausbeute 78.9%

1-Benzyl-3-(12-cyclohexyldodecyl)glycerine

Ausbeute 78.9%

Lösungsmittel

tetrahydrofuran

dimethylsulfoxide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONAfter the addition
2. 2
   workup.STIRRINGstirred at that temperature for 40 minutes
3. 3
   workup.STIRRINGthe resulting mixture is stirred at 60° C. for 2 hours
4. 4
   SonstigeThe thus obtaind reaction mixture
5. 5
   Extraktionextracted with hexane-ethyl acetate (1:1)
6. 6
   WaschenThe extract layer is washed with water
7. 7
   Sonstigedried
8. 8
   Einengenconcentrated
9. 9
   SonstigeThe residue is purified by silica gel column chromatography

Vorschrift

In 100 ml of dimethylsulfoxide is suspended 1.4 g of sodium hydride, to which 9.73 g of benzyl alcohol is added dropwise at room temperature with stirring. After the addition is over, the mixture is gradually heated to 60° C. and stirred at that temperature for 40 minutes. Then, a solution of 9.7 g of 1,2-epoxy-3-(12-cyclohexyldodecyloxy)propane in 50 ml of tetrahydrofuran is added dropwise to the mixture and the resulting mixture is stirred at 60° C. for 2 hours. The thus obtaind reaction mixture is then neutralized with dilute hydrochloric acid and extracted with hexane-ethyl acetate (1:1). The extract layer is washed with water, dried and concentrated. The residue is purified by silica gel column chromatography to yield 10.2 g of the captioned compound as an oily substance.

Quelle