Cyclooctanone → 2-Oxonanone

HRID 1694628Notes

Reaction equation

HRID 1694628 reaction equation
[C:1]1(=[O:9])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.ClC1C=CC=C(C(OO)=[O:18])C=1.C([O-])(O)=O.[Na+]>ClC(Cl)C>[O:18]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:1]1=[O:9]

Participants

5

Reactant 3

HCID 10403CyclooctanoneHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 1385682-OxonanoneYield 73.4%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

43.5 g (345 mmol) of cyclo-octanone is placed in solution in 430 ml of dichloroethane. 170 g (985 mmol) of meta-chloroperbenzoic acid is then added. The medium is heated to 80° C. for 48 hours. At room temperature, 400 ml of a Na2S2O5 and NaHCO3 saturated solution (1/1 v/v) are added. The medium is stirred vigorously for 18 hours. The organic phase is separated and contacted with Kl and H2O for 6 hours. The organic phase is separated and washed with a saturated solution of Na2S2O3, a saturated solution of NaCl then dried on MgSO4, filtered and concentrated under vacuum to give 36 g of the crude product.

Workup

  1. customThe organic phase is separated
  2. waitcontacted with Kl and H2O for 6 hours
  3. customThe organic phase is separated
  4. washwashed with a saturated solution of Na2S2O3
  5. dry with materiala saturated solution of NaCl then dried on MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-4087b6b08ee64c70acefa2fe8783a4eb
Source dataset
uspto-grants-2012_04
Patent number
US08158811B2

Reaction notes

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