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

HRID 1593242Notes

Reaction equation

HRID 1593242 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-fdd53a1c92bb4b9cb64cc2d12e71be1b
Source dataset
uspto-grants-2007_11
Patent number
US07294716B2

Reaction notes

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