4-Methoxybenzoic Acid → 3-(Chlorosulfonyl)-4-methoxybenzoic acid

HRID 2182901Notes

Reaction equation

HRID 2182901 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1.[Cl:12][S:13](O)(=[O:15])=[O:14]>O>[Cl:12][S:13]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:3]=1[O:2][CH3:1])[C:7]([OH:9])=[O:8])(=[O:15])=[O:14]

Participants

4

Reactant 2

HCID 74784-Methoxybenzoic AcidHCID 24638Chlorosulfonic acid

Product 1

HCID 38548883-(Chlorosulfonyl)-4-methoxybenzoic acidYield 66.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Solid 4-methoxy benzoic acid (45.6 g, 0.3 mol), in portions, was added to chlorosulfonic acid (139.8 g, 80 mL, 1.2 mol) at room temperature. After most of the bubbling had ceased, the reaction mixture was heated to 80° C. for 1 hr. The reaction mixture was then poured into vigorously stirring crushed-ice (500 g) and water was then added (500 mL). After 30 min, the white solid was collected, washed with water (2 L) and dried to give 50 g (66%) of the title compound.

Workup

  1. additionThe reaction mixture was then poured
  2. additionwas then added (500 mL)
  3. customthe white solid was collected
  4. washwashed with water (2 L)
  5. customdried

Sources & evidence

ORD record
ord-8beb80a7ede44fb6aa0f618066a9b71b
Source dataset
uspto-grants-2005_05
Patent number
US06897227B2

Reaction notes

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