Reaction #2348118

Reaction equation

(Z)-17-oxabicyclo[14.1.0]heptadec-8-ene

peracetic acid

(Z)-17-oxabicyclo[14.1.0]heptadec-8-ene

(E,E)-1,9-cyclohexadecadiene

(Z,Z)-1,9-cyclohexadecadiene

(E,Z)-1,9-cyclohexadecadiene

1,9-cyclohexadecadiene

sodium acetate

(E)-17-oxabicyclo[14.1.0]heptadec-8-ene

(E)-17-oxabicyclo[14.1.0]heptadec-8-ene

→

17-oxabicyclo[14.1.0]heptadec-8-ene

Solvents

methylene chloride

methylene chloride

Conditions

Workup

1. 1
   Extractionextracted once with methylene chloride
2. 2
   WashThe combined organic phases are washed with saturated NaCl solution
3. 3
   Dryingsubsequently dried with magnesium sulfate
4. 4
   Otherafter removal of the solvent 9.0 g of crude product
5. 5
   Otherare obtained
6. 6
   OtherAfter purification by chromatography with ethyl acetate/cyclohexane
7. 7
   Otheris obtained

Procedure

10 g 1,9-cyclohexadecadiene of the following composition are added to a solution of 14.1 g sodium acetate in 75 ml methylene chloride and the mixture is cooled to 0° C.: (Z,Z)-1,9-cyclohexadecadiene 18%, (E,Z)-1,9-cyclohexadecadiene 54%, (E,E)-1,9-cyclohexadecadiene 28%. 8.6 g peracetic acid (40% strength) in 15 ml methylene chloride are slowly added dropwise at this temperature and the mixture is subsequently stirred for three hours at 0° C. The reaction solution is poured on to ice-water and extracted once with methylene chloride. The combined organic phases are washed with saturated NaCl solution and subsequently dried with magnesium sulfate, and after removal of the solvent 9.0 g of crude product are obtained. After purification by chromatography with ethyl acetate/cyclohexane, a product having the following composition is obtained: (E)-17-oxabicyclo[14.1.0]heptadec-8-ene (1) 33%, (E)-17-oxabicyclo[14.1.0]heptadec-8-ene (2) 28%, (Z)-17-oxabicyclo[14.1.0]heptadec-8-ene (3) 21%, (Z)-17-oxabicyclo[14.1.0]heptadec-8-ene (4) 18%.

Source