m-Chloroperbenzoic acid → HCID 12094929, compound
Reaction equation
[C:1]1([C:6]2[CH:7]=[C:8]([CH:14]=[CH:15][CH:16]=2)[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:5][CH2:4][CH2:3][CH:2]=1.ClC1C=CC=C(C(OO)=[O:25])C=1>C(Cl)Cl>[C:1]12([C:6]3[CH:7]=[C:8]([CH:14]=[CH:15][CH:16]=3)[C:9]([O:11][CH2:12][CH3:13])=[O:10])[O:25][CH:5]1[CH2:4][CH2:3][CH2:2]2Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
5 g (23 mmol) of ethyl 3-cyclopent-1-ylbenzoate (4a) and 100 ml of methylene chloride are introduced into a round-bottomed flask. The solution is cooled to 0° C. and 9 g (28 mmol) of meta-chloroperbenzoic acid are added in portions. The mixture is stirred for 30 minutes at 0° C. and then for 4 hours at room temperature. The mixture is filtered. The filtrate is successively washed with a saturated aqueous sodium thiosulfate solution, a saturated aqueous sodium bicarbonate solution and then with a saturated aqueous sodium chloride solution. The organic phase is dried over Na2SO4, filtered and concentrated under reduced pressure. The residue is purified by flash chromatography on silica gel (cyclohexane/ethyl acetate: 95:5). The title product is obtained in the form of a colorless oil (4.8 g).
Workup
- waitfor 4 hours at room temperature
- filtrationThe mixture is filtered
- washThe filtrate is successively washed with a saturated aqueous sodium thiosulfate solution
- dry with materialThe organic phase is dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe residue is purified by flash chromatography on silica gel (cyclohexane/ethyl acetate: 95:5)
Sources & evidence
- ORD record
- ord-114d6c31fd0445bba403f7cd10b84145
- Source dataset
- uspto-grants-2007_01
- Patent number
- US07163957B2
Reaction notes
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