Peracetic Acid → 34748-97-5

HRID 2260936Notes

Reaction equation

HRID 2260936 reaction equation
[CH:1]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH:10]=[CH:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.C([O-])(=[O:19])C.[Na+].C1=CCCCCCCC=CCCCCCC1.C1=CCCCCCCC=CCCCCCC1.C1=CCCCCCCC=CCCCCCC1.C(OO)(=O)C.C12OC1CCCCCCC=CCCCCCC2.C12OC1CCCCCCC=CCCCCCC2>C(Cl)Cl>[CH:1]12[O:19][CH:16]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][CH2:2]2

Participants

10

Reactant 8

HCID 6585Peracetic AcidHCID 517045Sodium AcetateHCID 5348701,9-CyclohexadecadieneHCID 5362807110028-14-3HCID 60330601,9-Cyclohexadecadiene, (E,Z)-HCID 1983853617-Oxabicyclo[14.1.0]heptadec-8-ene2×HCID 441481964277-06-9HCID 5684187934748-97-52×

Product 1

HCID 5423085934748-97-5

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

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%.

Workup

  1. extractionextracted once with methylene chloride
  2. washThe combined organic phases are washed with saturated NaCl solution
  3. dry with materialsubsequently dried with magnesium sulfate
  4. customafter removal of the solvent 9.0 g of crude product
  5. customare obtained
  6. customAfter purification by chromatography with ethyl acetate/cyclohexane
  7. customis obtained

Sources & evidence

ORD record
ord-3ea3f627ac084da6bafffe4eb0b664e5
Source dataset
uspto-grants-2010_12
Patent number
US07846886B2

Reaction notes

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