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

HRID 35153Notes

Reaction equation

HRID 35153 reaction equation
[CH:1]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH:9]=[CH:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[C:16]([O-:19])(=[O:18])[CH3:17].[Na+].O.C(OO)(=[O:24])C>C(Cl)Cl>[CH:1]12[O:18][CH:15]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH:8]=[CH:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2.[CH:16]12[O:19][CH:1]1[CH:2]1[O:24][CH:3]1[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:17]2

Participants

7

Reactant 4

HCID 962WaterHCID 6585Peracetic AcidHCID 517045Sodium AcetateHCID 53656773Cyclopentadeca-1,8-diene

Product 2

HCID 5410369416-Oxa-bicyclo-[13.1.0]-hexadec-7-eneHCID 86742341Cyclopentadecadiene dioxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  1. additionis added dropwise within 2 hours
  2. customis 2° C
  3. stirringSubsequently, stirring
  4. stirringAfter another 2 hours of stirring at room temperature
  5. washthe reaction mixture is washed first with 5×100 ml water, subsequently with 100 ml 5% by wt. sodium bicarbonate solution
  6. customSubsequently, the phases are separated
  7. dry with materialThe organic phase is dried over sodium sulfate
  8. customAfter removing the solvent
  9. distillationthe product mixture is subjected to fractional distillation

Sources & evidence

ORD record
ord-574677b32f6844ccabc69aa55ceee374
Source dataset
uspto-grants-1988_08
Patent number
US04766107

Reaction notes

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