Water → 16-Oxa-bicyclo-[13.1.0]-hexadec-7-ene

Participants

Reaction Steps

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.

Provenance & Evidence