Chlorosulfonic acid → 4-(2-Methoxy-1-methoxymethyl-ethoxy)-benzenesulfonyl chloride
Reaction equation
[CH3:1][O:2][CH2:3][CH:4]([CH2:12][O:13][CH3:14])[O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[Cl:15][S:16](O)(=[O:18])=[O:17]>C(Cl)(Cl)Cl>[CH3:1][O:2][CH2:3][CH:4]([CH2:12][O:13][CH3:14])[O:5][C:6]1[CH:11]=[CH:10][C:9]([S:16]([Cl:15])(=[O:18])=[O:17])=[CH:8][CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -30 °C
Procedure
(2-Methoxy-1-methoxymethyl-ethoxy)-benzene (1.0 g) was dissolved in 10 mL of chloroform and the solution was cooled to −30° C. Chlorosulfonic acid (1 mL) was added dropwise while maintaining the temperature of the mixture below −20° C. Stirring was continued in succession for one hour at −20° C., for one hour at 5° C. and for 30 minutes at room temperature. The mixture was poured on ice, the organic layer washed with cold water, dried (sodium sulfate) and concentrated yielding 0.8 g of 4-(2-methoxy-1-methoxymethyl-ethoxy)-benzenesulfonyl chloride as an oil. EI-MS: 294 (M+).
Workup
- temperaturewhile maintaining the temperature of the mixture below −20° C
- additionThe mixture was poured on ice
- washthe organic layer washed with cold water
- dry with materialdried (sodium sulfate)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-7ffdee41af59488b8b363df8c771e915
- Source dataset
- uspto-grants-2004_09
- Patent number
- US06797710B2
Reaction notes
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