Chlorine → 1-[3-Chloro-4-(3,3,5,5-tetramethylcyclohexyl)phenyl]ethanone
Reaction equation
[Cl-:1].[Al+3].[Cl-].[Cl-].[CH3:5][C:6]1([CH3:23])[CH2:11][C:10]([CH3:13])([CH3:12])[CH2:9][CH:8]([C:14]2[CH:19]=[CH:18][C:17]([C:20](=[O:22])[CH3:21])=[CH:16][CH:15]=2)[CH2:7]1.ClCl>ClCCl>[Cl:1][C:15]1[CH:16]=[C:17]([C:20](=[O:22])[CH3:21])[CH:18]=[CH:19][C:14]=1[CH:8]1[CH2:7][C:6]([CH3:23])([CH3:5])[CH2:11][C:10]([CH3:12])([CH3:13])[CH2:9]1Participants
Conditions
- Temperature
- 0 °C
Procedure
40.25 g of aluminium chloride are added at 0° C., under an inert atmosphere, to 350 ml of dichloromethane, followed by addition of 5 g of 1-[4-(3,3,5,5-tetramethylcyclohexyl)phenyl]ethanone (compound V.1) dissolved in dichloromethane. After stirring for 2 hours at 0° C., 17.1 ml of chlorine gas (d=1.565, measured in the liquid state at −78° C.) are bubbled into the reaction. After warming to room temperature, a water/ice mixture is added to the reaction mixture. The resulting mixture is extracted with dichloromethane, the phases are separated after settling has taken place, and the organic phase is dried over magnesium sulphate and concentrated under reduced pressure. The residue is purified on a column of silica gel, eluting with a 7/3 (v/v) cyclohexane/dichloromethane mixutre; yield=74%; m.p.=64° C.
Workup
- custommeasured in the liquid state at −78° C.
- customare bubbled into the reaction
- temperatureAfter warming to room temperature
- additiona water/ice mixture is added to the reaction mixture
- extractionThe resulting mixture is extracted with dichloromethane
- customthe phases are separated after settling
- dry with materialthe organic phase is dried over magnesium sulphate
- concentrationconcentrated under reduced pressure
- customThe residue is purified on a column of silica gel
- washeluting with a 7/3 (v/v) cyclohexane/dichloromethane mixutre
Sources & evidence
- ORD record
- ord-8d60e7d78c004558bd93730df4572b87
- Source dataset
- uspto-grants-2002_11
- Patent number
- US06482986B1
Reaction notes
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