Methanol → Methyl 2-chloro-4-(methylsulfonyl)benzoate

HRID 1499239Notes

Reaction equation

HRID 1499239 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([S:11]([CH3:14])(=[O:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[CH3:20]O>>[Cl:1][C:2]1[CH:10]=[C:9]([S:11]([CH3:14])(=[O:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:20])=[O:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 7358632-Chloro-4-(methylsulfonyl)benzoic acid

Product 1

HCID 66968682Methyl 2-chloro-4-(methylsulfonyl)benzoate

Procedure

To a mixture of 2-chloro-4-(methylsulfonyl)benzoic acid (5 g, 21.3 mmol) in anhydrous methanol (100 mL) was added concentrated sulfuric acid (0.5 mL). The resulting solution was stirred for 18 h at reflux. Upon cooling, the mixture was concentrated under reduced pressure, dissolved in CH2Cl2 and washed with NaHCO3 solution and brine. The organic phase was dried over sodium sulfate and concentrated to afford methyl 2-chloro-4-(methylsulfonyl)benzoate as a white solid.

Workup

  1. temperatureat reflux
  2. temperatureUpon cooling
  3. concentrationthe mixture was concentrated under reduced pressure
  4. dissolutiondissolved in CH2Cl2
  5. washwashed with NaHCO3 solution and brine
  6. dry with materialThe organic phase was dried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-197efc6fead946b295778c89cc5c68ea
Source dataset
uspto-grants-2015_12
Patent number
US09199994B2

Reaction notes

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