Cyclooctanone → 2-Oxonanone
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
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
43.5 g (345 mmol) of cyclooctanone (compound of formula (VI) with n=6) (ACROS) are placed in solution in 430 ml of dichloroethane. 170 g (985 mmol) of meta-chloroperbenzoic acid are 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 strongly stirred for 18 hours. The organic phase is separated and placed into the presence of KI and H2O for 6 hours. The organic phase is separated and washed with a Na2S2O3 saturated solution, with a NaCl saturated solution, and is then dried on MgSO4, filtered and concentrated in vacuo in order to obtain 36 g of crude product.
Workup
- customThe organic phase is separated
- waitplaced into the presence of KI and H2O for 6 hours
- customThe organic phase is separated
- washwashed with a Na2S2O3 saturated solution, with a NaCl saturated solution
- customis then dried on MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo in order
Sources & evidence
- ORD record
- ord-692924524aaf452e94790668f1f41bf8
- Source dataset
- uspto-grants-2011_04
- Patent number
- US07928254B2
Reaction notes
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