Réaction #1198

Équation de réaction

tetradecanol

NaH

methallyl chloride

m-chloroperbenzoic acid

→

1,2-epoxy-2-methyl-3-tetradecyloxypropane

Rendement 79.5%

Solvants

water

dimethylformamide

dichloromethane

Conditions de réaction

Traitement

1. 1
   AutreA 200-ml flask equipped with a stirrer
2. 2
   AutreAfter completion of the reaction
3. 3
   Extractionsubjected to extraction with hexane
4. 4
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
5. 5
   workup.ADDITIONThe resultant residue was charged into a 300-ml flask
6. 6
   Autreequipped with a stirrer
7. 7
   AutreSolids formed
8. 8
   Autrewere separated by filtration
9. 9
   Concentrationthe resultant solution was concentrated under reduced pressure
10. 10
    Autrepurified by column chromatography on silica gel

Mode opératoire

A 200-ml flask equipped with a stirrer was charged with 10 g (46.6 mmol) of tetradecanol, 50 ml of dimethylformamide, 2.86 g (71.5 mmol) of 60% NaH and 5.96 g (65.8 mmol) of methallyl chloride. The contents were stirred at 60° C. for 15 hours. After completion of the reaction, the reaction mixture was added with water and subjected to extraction with hexane, and the solvent was distilled off under reduced pressure. The resultant residue was charged into a 300-ml flask equipped with a stirrer, and 12.24 g (70.9 mmol) of m-chloroperbenzoic acid and 200 ml of dichloromethane were added thereto. The resultant mixture was stirred at room temperature for 19 hours. Solids formed were separated by filtration, and the resultant solution was concentrated under reduced pressure and then purified by column chromatography on silica gel, thereby obtaining 10.54 g (yield: 79.4%) of 1,2-epoxy-2-methyl-3-tetradecyloxypropane as an intermediate.

Source