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

HRID 2251181Notes

Reaction equation

HRID 2251181 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-a15361d764aa4026bab35c5e579d787c
Source dataset
uspto-grants-2008_01
Patent number
US07319099B2

Reaction notes

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