Chlorobenzene → Benzene, 1,1'-sulfonylbis-, dichloro deriv.

HRID 2351106Notes

Reaction equation

Cl[S:2]([OH:5])(=O)=[O:3].S(Cl)(Cl)=O.[Cl:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[CH:15]1[CH:16]=[C:11]([Cl:10])[CH:12]=[C:13]([S:2]([C:13]2[CH:14]=[CH:15][CH:16]=[C:11]([Cl:10])[CH:12]=2)(=[O:5])=[O:3])[CH:14]=1

Participants

Reactant 3

HCID 7964Chlorobenzene

HCID 24386Thionyl Chloride

HCID 24638Chlorosulfonic acid

Product 1

HCID 3037034Benzene, 1,1'-sulfonylbis-, dichloro deriv.Yield 197.3%

Conditions

Temperature: 195 °C

Procedure

The filtrate from Example 1 is freed from methoanol by distillation, the residue is returned to the reaction vessel, and 562.5 g (5 mol) of chlorobenzene is added. chlorobenzenesulfonic acid chloride is formed by adding 476 g (4 mol) of chlorosulfonic acid and 466 g (4 mol) of thionyl chloride, the mixture is heated to 195° C., and 337.5 g (3 mol) of chlorobenzene is added at such a rate that the temperature does not fall. the charge is subsequently treated as described in Example 1, giving 850 g (74% yield) of dichlorodiphenyl sulfone of melting point 149°-150° C. Gas-chromatographic analysis of the product gives 99.6% 4,4'-isomer, 0.3% 2,4'-isomer, and 0.1% 3,4'-isomer.

Workup

additionthe charge is subsequently treated

Sources & evidence

ORD record: ord-cefd6b2212304d3691e1ad736c296592
Source dataset: uspto-grants-1989_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04871876

Reaction notes

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