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

HRID 356939Notes

Reaction equation

HRID 356939 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-b4dc8474cf184bdaa9771d2c876fed48
Source dataset
uspto-grants-1998_11
Patent number
US05840724

Reaction notes

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