p-Toluenesulfonic acid monohydrate → Methyl 2,2-dichloro-12-(4-chlorophenyl)-11-dodecenoate
Reaction equation
[Cl:1][C:2]([Cl:25])([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1)O)[C:3]([O:5][CH3:6])=[O:4].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Cl:25][C:2]([Cl:1])([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH:15]=[CH:16][C:18]1[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=1)[C:3]([O:5][CH3:6])=[O:4]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
Methyl 2,2-dichloro-12-(4-chlorophenyl)-12-hydroxydodecanoate (8.89 g, 21.91 mmol) was dissolved in 300 ml of toluene. The solution was added with p-toluenesulfonic acid monohydrate (1.67 g, 8.78 mmol), and stirred at 80° C. for 4 hours. The reaction mixture was washed with 200 mL of water and 10 ml of aqueous saturated sodium hydrogencarbonate. The aqueous layer was further extracted with 100 mL of ethyl acetate. The organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. The extracts were purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/1). The solvent was evaporated under reduced pressure to obtain the desired compound (8.38 g, yield 97.6%) as yellow oil.
Workup
- washThe reaction mixture was washed with 200 mL of water and 10 ml of aqueous saturated sodium hydrogencarbonate
- extractionThe aqueous layer was further extracted with 100 mL of ethyl acetate
- washwashed with saturated brine
- dry with materialdried over anhydrous sodium sulfate
- customThe extracts were purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/1)
- customThe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-c5ae4846b5154274a55a8eeaeeef1444
- Source dataset
- uspto-grants-2006_09
- Patent number
- US07109242B2
Reaction notes
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