4-Toluenesulfonyl chloride → 2-(4-Chlorophenyl)ethyl 4-methylbenzenesulfonate
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=1.[C:11]1([CH3:21])[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1>N1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][O:10][S:17]([C:14]2[CH:15]=[CH:16][C:11]([CH3:21])=[CH:12][CH:13]=2)(=[O:19])=[O:18])=[CH:4][CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
5 g (31.9 mmol) of 2-(4-Chloro-phenyl)-ethanol was dissolved in 100 ml of pyridine and the solution was cooled to 0° C. 6.09 g (31.9 mmol) of para-toluene sulfonyl chloride was added to this solution and the reaction was stirred at 0° C. for 2 h, then at room temperature for 16 h. The solvent was removed under reduced pressure, the residue was taken-up in ethyl acetate and the solution was washed once with saturated aqueous sodium bicarbonate, once with water, and once with saturated aqueous sodium chloride. The organic phase was dried with sodium sulfate, filtered and the solvent was removed under reduced pressure. The compound was recrystallised from n-heptane/ethyl acetate. Yield: 6.23 g MS (Cl+): m/e=311, chloro pattern.
Workup
- waitat room temperature for 16 h
- customThe solvent was removed under reduced pressure
- washthe solution was washed once with saturated aqueous sodium bicarbonate, once with water
- dry with materialThe organic phase was dried with sodium sulfate
- filtrationfiltered
- customthe solvent was removed under reduced pressure
- customThe compound was recrystallised from n-heptane/ethyl acetate
Sources & evidence
- ORD record
- ord-ee503523bcac4ab9b6990f9d2c56b2d0
- Source dataset
- uspto-grants-2005_06
- Patent number
- US06906084B2
Reaction notes
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