Lithium hydroxide, monohydrate → 3-Chloro-5-methanesulfonylbenzoic acid

HRID 403402Notes

Reaction equation

HRID 403402 reaction equation
C[O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([S:10]([CH3:13])(=[O:12])=[O:11])[CH:7]=[C:6]([Cl:14])[CH:5]=1.O.[OH-].[Li+]>O1CCCC1.O>[Cl:14][C:6]1[CH:5]=[C:4]([CH:9]=[C:8]([S:10]([CH3:13])(=[O:12])=[O:11])[CH:7]=1)[C:3]([OH:15])=[O:2]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 18952494Methyl 3-chloro-5-(methylsulfonyl)benzoate

Product 1

HCID 189525313-Chloro-5-methanesulfonylbenzoic acidYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-chloro-5-methanesulfonyl-benzoic acid methyl ester (2.3 g, 9.25 mmol) in tetrahydrofuran (30 mL) and water (15 mL) was added lithium hydroxide monohydrate (1.164 g, 27.75 mmol) at 25° C. and the reaction mixture was stirred for 1 h. The solvent was evaporated, the residue dissolved in water (25 mL), acidified with 2M aqueous hydrochloric acid to pH 3 and extracted three times with ethyl acetate (40 mL each). The combined organic layers were washed with brine (50 mL), dried over anhydrous sodium sulfate and evaporated to afford the desired compound as a colorless solid (1.8 g, 83%). MS (ESI−): m/z=233.2 ([M−H]−).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in water (25 mL)
  3. extractionextracted three times with ethyl acetate (40 mL each)
  4. washThe combined organic layers were washed with brine (50 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-d480bf84b80542d7bcf9c29e30f10b1e
Source dataset
uspto-grants-2014_06
Patent number
US08748434B2

Reaction notes

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