Lithium hydroxide, monohydrate → HCID 59662623, compound

HRID 545307Notes

Reaction equation

HRID 545307 reaction equation
C([O:3][C:4](=[O:21])[C:5]([CH3:20])([S:7]([C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=1)(=[O:9])=[O:8])[CH3:6])C.O.[OH-].[Li+]>C1COCC1.O.O>[CH3:20][C:5]([S:7]([C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:18])([F:19])[F:17])=[CH:12][CH:11]=1)(=[O:9])=[O:8])([CH3:6])[C:4]([OH:21])=[O:3]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 58198514HCID 58198514, compound

Product 1

HCID 59662623HCID 59662623, compoundYield 83.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of 15.3 g (47 mmol) of 2-methyl-2-(4-trifluoromethyl-benzenesulfonyl)-propionic acid ethyl ester in THF/water (4/1, 160 mL) were added 3.95 g (94 mmol) of lithium hydroxide monohydrate. The reaction was stirred at room temperature for 18 h. The reaction was further diluted with water (60 mL) and then washed with DCM (2×40 mL). The basic aqueous layer was cooled in an ice bath and then acidified with 1N aqueous HCl solution to pH 2. The acidic aqueous layer was extracted with DCM (3×60 mL). The combined organic extracts were washed with brine, dried over Na2SO4 and filtered. Concentration of the filtrate under reduced pressure afforded 11.6 g of 2-methyl-2-(4-trifluoromethyl -benzenesulfonyl)-propionic acid.

Workup

  1. washwashed with DCM (2×40 mL)
  2. temperatureThe basic aqueous layer was cooled in an ice bath
  3. extractionThe acidic aqueous layer was extracted with DCM (3×60 mL)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered

Sources & evidence

ORD record
ord-4fdba060083647a891bc658d9ae0507b
Source dataset
uspto-grants-2011_05
Patent number
US07935715B2

Reaction notes

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