Chlorine monoxide → 2-(1-Chloroethyl)benzenesulfonyl chloride

HRID 4139

Reaction equation

HRID 4139 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([Cl:12])(=[O:11])=[O:10])[CH3:2].O(Cl)[Cl:14]>C(Cl)(Cl)(Cl)Cl>[Cl:14][CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([Cl:12])(=[O:11])=[O:10])[CH3:2]

Participants

4

Reactant 2

HCID 24646Chlorine monoxideHCID 27373732-Ethylbenzenesulfonyl chloride

Product 1

HCID 133646252-(1-Chloroethyl)benzenesulfonyl chlorideYield 83.9%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

A solution of 2-ethylbenzenesulfonyl chloride (obtained by chlorosulfonation of ethylbenzene) (7.78 g) in carbon tetrachloride (5.0 ml) was contacted with a solution of dichlorine monoxide (82 mmol) in carbon tetrachloride (100 ml) and the mixture was heated in a closed system at 50°-60° for 16 hrs. The mixture was dried (MgSO4) and volatiles were removed under vacuum. The residue was kugelrohr distilled to give 7.63 g of colorless oil, bp 75°-80° (0.15 mm). 1H nmr δCDCl3TMS 8.20-7.35 (m). 6.13 (q, J=7 Hz), 1.90 (d, J=7 Hz).

Workup

  1. temperaturethe mixture was heated in a closed system at 50°-60° for 16 hrs
  2. dry with materialThe mixture was dried (MgSO4) and volatiles
  3. customwere removed under vacuum
  4. distillationThe residue was kugelrohr distilled

Sources & evidence

ORD record
ord-5a26a82ee29e4183bd849568dc3c6a8f
Source dataset
uspto-grants-1988_02
Patent number
US04723990

Linked notes

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