반응 #63431

반응 방정식

H2O

cyclopentadeca-1,8-diene

peracetic acid

sodium acetate

→

desired product

16-oxa-bicyclo-[13.1.0]-hexadec-7-ene

cyclopentadecadiene dioxide

용매

methylene chloride

반응 조건

후처리

1. 1
   workup.ADDITIONis added dropwise within 2 hours
2. 2
   기타is 2° C
3. 3
   workup.STIRRINGSubsequently, stirring
4. 4
   workup.STIRRINGAfter another 2 hours of stirring at room temperature
5. 5
   세척the reaction mixture is washed first with 5×100 ml water, subsequently with 100 ml 5% by wt. sodium bicarbonate solution
6. 6
   기타Subsequently, the phases are separated
7. 7
   건조The organic phase is dried over sodium sulfate
8. 8
   기타After removing the solvent
9. 9
   workup.DISTILLATIONthe product mixture is subjected to fractional distillation

실험 절차

To a mixture consisting of 100 g (0.49 moles) cyclopentadeca-1,8-diene, 217 g (1.6 moles) sodium acetate×3 H2O and 1000 ml methylene chloride, 78 ml 40% by wt. (0.47 moles) peracetic acid is added dropwise within 2 hours under stirring. The reaction temperature is 2° C. Subsequently, stirring is continued for another 30 minutes at the same temperature and the mixture is subsequently heated to room temperature. After another 2 hours of stirring at room temperature, the reaction mixture is washed first with 5×100 ml water, subsequently with 100 ml 5% by wt. sodium bicarbonate solution, and finally with 100 ml saturated sodium chloride solution and thus rendered neutral and free from peroxide. Subsequently, the phases are separated. The organic phase is dried over sodium sulfate. After removing the solvent, the product mixture is subjected to fractional distillation. 53 grams of the desired product is obtained in additon to 35 g initial substance (cyclopentadeca-1,8 -diene) and 11 g cyclopentadecadiene dioxide.

출처