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

HRID 1870389Notes

Reaction equation

HRID 1870389 reaction equation
[C:1]([OH:11])(=[O:10])[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[Cl:12][S:13](O)(=[O:15])=[O:14]>>[Cl:12][S:13]([C:6]1[CH:7]=[C:2]([CH:3]=[CH:4][C:5]=1[O:8][CH3:9])[C:1]([OH:11])=[O:10])(=[O:15])=[O:14]

Participants

3

Reactant 2

HCID 74784-Methoxybenzoic AcidHCID 24638Chlorosulfonic acid

Product 1

HCID 38548883-(Chlorosulfonyl)-4-methoxybenzoic acid

Conditions

Temperature
90 °C

Procedure

A stirred solution of chlorosulfonic acid (90 mL) at room temperature is treated with p-anisic acid (40 g), portionwise, during 30 minutes. When the addition is complete, the mixture is stirred at 90° C. for 75 minutes, then it is cooled and poured onto ice. The white precipitate is collected and dissolved in ethyl acetate (300 mL). The organic extract is washed with brine (2×250 mL), dried over magnesium sulfate, and concentrated, to give 3-chlorosulfonyl-4-methoxybenzoic acid (34 g), in the form of a white solid m.p. 168-170° C.

Workup

  1. additionWhen the addition
  2. temperatureit is cooled
  3. additionpoured onto ice
  4. customThe white precipitate is collected
  5. dissolutiondissolved in ethyl acetate (300 mL)
  6. extractionThe organic extract
  7. washis washed with brine (2×250 mL)
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-2e840bec4c76452fa29b19aa4f5a82ca
Source dataset
uspto-grants-2000_08
Patent number
US06096768

Reaction notes

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