m-Chloroperbenzoic acid → HCID 68467373, compound
Reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[CH2:12]([C:14]1[CH:19]=[C:18]([CH3:20])[CH:17]=[C:16]([CH2:21][CH3:22])[C:15]=1[CH:23]1[C:28](=[O:29])[CH2:27][CH:26]([CH2:30][CH:31]([S:33][CH2:34][CH3:35])[CH3:32])[CH2:25][C:24]1=[O:36])[CH3:13]>ClCCl>[CH2:21]([C:16]1[CH:17]=[C:18]([CH3:20])[CH:19]=[C:14]([CH2:12][CH3:13])[C:15]=1[CH:23]1[C:24](=[O:36])[CH2:25][CH:26]([CH2:30][CH:31]([S:33]([CH2:34][CH3:35])=[O:6])[CH3:32])[CH2:27][C:28]1=[O:29])[CH3:22]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of 70% 3-chloroperoxybenzoic acid (0.104 g, 0.42 mmol) in dichloromethane (2 ml) is added dropwise to a solution of 2-(2,6-diethyl-4-methylphenyl)-5-[2-(ethylthio)propyl]cyclo-hexane-1,3-dione (0.17 g, 0.47 mmol) in dichloromethane (3 ml) at 0° C. and the reaction mixture is stirred for 1 hour at 0° C. and then left to stand at room temperature overnight. The reaction mixture is diluted with dichloromethane, washed with 15% aqueous sodium metabisulfite solution and brine, dried over anhydrous magnesium sulfate, filtered and the filtrate evaporated in vacuo. The residue is purified by column chromatography on silica gel to give 2-(2,6-diethyl-4-methylphenyl)-5-[2-(ethylsulfinyl)propyl]cyclohexane-1,3-dione, m.p. 58-61° C.
Workup
- waitleft
- waitto stand at room temperature overnight
- washwashed with 15% aqueous sodium metabisulfite solution and brine
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- customthe filtrate evaporated in vacuo
- customThe residue is purified by column chromatography on silica gel
Sources & evidence
- ORD record
- ord-f13c21e6d4824decb2fbb16f1c4385e1
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08084649B2
Reaction notes
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