2-Chlorobenzoic Acid → Benzoic acid, 2-chloro-5-(chlorosulfonyl)-

HRID 1533441Notes

Reaction equation

HRID 1533441 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[Cl:11][S:12](O)(=[O:14])=[O:13]>>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([S:12]([Cl:11])(=[O:14])=[O:13])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

3

Reactant 2

HCID 83742-Chlorobenzoic AcidHCID 24638Chlorosulfonic acid

Product 1

HCID 67306Benzoic acid, 2-chloro-5-(chlorosulfonyl)-Yield 87.1%

Conditions

Temperature
95 °C

Procedure

Commerically available 2-chlorobenzoic acid (80.0 g), (0.5 mol), was added portionwise to chlorosulphonic acid (320 g) with vigorous stirring. The reaction was heated to 95° C. for 6 hrs then cooled overnight to room temperature. The solution was quenched onto ice/water (1.5 kg/324 ml) and stirred for 15 min. The precipitated product was filtered, water washed and dried at 50° C. in vacuo, to give the title compound (111.1 g, 85.2%) as a white solid with m.p. 140° C. δ (CDCl3): 7.42 (1H,m), 8.27 (1H,m), 8.75 (1H,m).

Workup

  1. temperaturethen cooled overnight to room temperature
  2. customThe solution was quenched onto ice/water (1.5 kg/324 ml)
  3. filtrationThe precipitated product was filtered
  4. washwater washed
  5. customdried at 50° C. in vacuo

Sources & evidence

ORD record
ord-36d3e56861024634a9b17faa422bc616
Source dataset
uspto-grants-2001_03
Patent number
US06207829B1

Reaction notes

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