2,6-Dichlorobenzoic acid → 2,6-dichloro-3-chlorosulfonyl-benzoic Acid

HRID 1602776Notes

Reaction equation

HRID 1602776 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:3]=1[C:4]([OH:6])=[O:5].[Cl:12][S:13](O)(=[O:15])=[O:14]>>[Cl:12][S:13]([C:8]1[C:7]([Cl:11])=[C:3]([C:2]([Cl:1])=[CH:10][CH:9]=1)[C:4]([OH:6])=[O:5])(=[O:15])=[O:14]

Participants

3

Reactant 2

HCID 57582,6-Dichlorobenzoic acidHCID 24638Chlorosulfonic acid

Product 1

HCID 35382162,6-dichloro-3-chlorosulfonyl-benzoic AcidYield 61%

Conditions

Temperature
10 °C

Procedure

Part A: Under an atmosphere of nitrogen gas, a reaction vessel was charged with 2,6-dichlorobenzoic acid (10 g, 53.55 mmol) (Formula F) and chlorosulfonic acid (3 ml, 472 mmol). The reaction mixture was refluxed for 1 hour and cooled to 10° C. The contents of the reaction vessel were poured slowly into 3 L of ice water. The white solid which precipitated was collected by filtration and dried in vacuo (10 mm) at 35° C. for 48 hours to give 3-(chlorosulfonyl)-2,6-dichlorobenzoic acid (Formula G) (9.2 g, 61% yield).

Workup

  1. temperatureThe reaction mixture was refluxed for 1 hour
  2. customThe white solid which precipitated
  3. filtrationwas collected by filtration
  4. customdried in vacuo (10 mm) at 35° C. for 48 hours

Sources & evidence

ORD record
ord-ef35d581478f48a09743570f9b87e1cd
Source dataset
uspto-grants-1999_11
Patent number
US05985838

Reaction notes

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