Reaction #1198

Reaction equation

tetradecanol

NaH

methallyl chloride

m-chloroperbenzoic acid

→

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

Yield 79.5%

Solvents

water

dimethylformamide

dichloromethane

Conditions

Workup

1. 1
   OtherA 200-ml flask equipped with a stirrer
2. 2
   OtherAfter 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
   Otherequipped with a stirrer
7. 7
   OtherSolids formed
8. 8
   Otherwere separated by filtration
9. 9
   Concentrationthe resultant solution was concentrated under reduced pressure
10. 10
    Otherpurified by column chromatography on silica gel

Procedure

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