Hydrochloric Acid → 5-Methanesulfonyl-2-(2,2,3,3,3-pentafluoro-propoxy)-benzoic acid

HRID 1820726Notes

Reaction equation

HRID 1820726 reaction equation
C[O:2][C:3](=[O:23])[C:4]1[CH:9]=[C:8]([S:10]([CH3:13])(=[O:12])=[O:11])[CH:7]=[CH:6][C:5]=1[O:14][CH2:15][C:16]([F:22])([F:21])[C:17]([F:20])([F:19])[F:18].O.[OH-].[Li+].Cl>C1COCC1.O>[CH3:13][S:10]([C:8]1[CH:7]=[CH:6][C:5]([O:14][CH2:15][C:16]([F:21])([F:22])[C:17]([F:18])([F:19])[F:20])=[C:4]([CH:9]=1)[C:3]([OH:23])=[O:2])(=[O:12])=[O:11]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 866007065-Methanesulfonyl-2-(2,2,3,3,3-pentafluoro-propoxy)-benzoic acid methyl ester

Product 1

HCID 211003155-Methanesulfonyl-2-(2,2,3,3,3-pentafluoro-propoxy)-benzoic acidYield 92.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 5-methanesulfonyl-2-(2,2,3,3,3-pentafluoro-propoxy)-benzoic acid methyl ester (414 mg) in THF (5 mL) was added a solution of lithium hydroxide monohydrate (72 mg) in water (5 mL), and the reaction mixture was stirred at room temperature for 1 hour. After such time 1.72 mL of 1N aqueous hydrochloric acid solution was added. The reaction mixture was then concentrated in vacuo, and the resulting precipitate was then washed several times with water to yield the title compound as a white solid (367 mg). MS (m/e): 347.1 (M−H, 100%).

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. washthe resulting precipitate was then washed several times with water

Sources & evidence

ORD record
ord-df85105c770546ba9f725c016dd75afb
Source dataset
uspto-grants-2009_10
Patent number
US07605163B2

Reaction notes

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