Cumene → 4-(Propan-2-yl)benzene-1-sulfonyl chloride
Reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[Cl:10][S:11](O)(=[O:13])=[O:12].[Cl-].[NH4+]>C(Cl)Cl>[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([S:11]([Cl:10])(=[O:13])=[O:12])=[CH:6][CH:5]=1)([CH3:3])[CH3:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 5 °C
Procedure
A solution of 11.6 ml of isopropylbenzene in 100 ml of methylene chloride was added at 5° C. within 30 minutes to 18.3 ml of chlorosulfonic acid. The reaction mixture was stirred at 5° C. for 1 hour, poured on to 500 ml of ice-water and, after stirring for 5 minutes, treated with 100 g of ammonium chloride. After extraction with methylene chloride (1×800 ml, 1×500 ml) the organic phases were combined, dried with magnesium sulphate and the solvent was removed on a rotary evaporator. 12.3 g of 4-isopropyl-benzenesulfonyl chloride separated as a reddish oil, which was used without further purification.
Workup
- stirringafter stirring for 5 minutes
- extractionAfter extraction with methylene chloride (1×800 ml, 1×500 ml) the organic phases
- dry with materialdried with magnesium sulphate
- customthe solvent was removed on a rotary evaporator
- custom12.3 g of 4-isopropyl-benzenesulfonyl chloride separated as a reddish oil, which
- customwas used without further purification
Sources & evidence
- ORD record
- ord-9271afe45318454fb5438306f93af6d4
- Source dataset
- uspto-grants-1999_09
- Patent number
- US05958910
Reaction notes
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