Benzoic Acid → Benzoic acid, 3-(chlorosulfonyl)-

HRID 2182905Notes

Reaction equation

HRID 2182905 reaction equation
[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:10][S:11](O)(=[O:13])=[O:12]>>[Cl:10][S:11]([C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=1)[C:1]([OH:9])=[O:8])(=[O:13])=[O:12]

Participants

3

Reactant 2

HCID 243Benzoic AcidHCID 24638Chlorosulfonic acid

Product 1

HCID 77641Benzoic acid, 3-(chlorosulfonyl)-Yield 80.1%

Conditions

Temperature
127.5 °C

Procedure

Solid benzoic acid (50 g, 0.41 mol) in portions was added to chlorosulfonic acid (348.7 g, 200 mL, 3 mol) at room temperature. The reaction mixture was heated to 125-130° C. for 2 hr and was then poured into vigorously stirred crushed-ice (1000 g). After 30 min, the white solid was collected, washed with water (1 L) and air dried to give 72.5 g (80%) of the title compound.

Workup

  1. additionwas then poured
  2. customthe white solid was collected
  3. washwashed with water (1 L) and air
  4. customdried

Sources & evidence

ORD record
ord-cdc5a7968e91482ab5e5bfd416bd9b14
Source dataset
uspto-grants-2005_05
Patent number
US06897227B2

Reaction notes

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