Lithium hydroxide, monohydrate → 2-Methanesulfonyl-2-methylpropanoic acid

HRID 73232Notes

Reaction equation

HRID 73232 reaction equation
C([O:3][C:4](=[O:12])[C:5]([S:8]([CH3:11])(=[O:10])=[O:9])([CH3:7])[CH3:6])C.O.[OH-].[Li+]>C1COCC1.O.O>[CH3:11][S:8]([C:5]([CH3:7])([CH3:6])[C:4]([OH:12])=[O:3])(=[O:10])=[O:9]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 58287607HCID 58287607, compound

Product 1

HCID 2132402-Methanesulfonyl-2-methylpropanoic acidYield 95.6%

Reagents, catalysts & solvents 2

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

Procedure

To a solution of 500 mg (2.6 mmol) of 2-methanesulfonyl-2-methyl-propionic acid ethyl ester in THF/water (4/1, 5 mL) were added 270 mg (6.6 mmol) of lithium hydroxide monohydrate. The reaction was stirred at room temperature for 18 h. The reaction was further diluted with water (20 mL) and then washed with DCM (2×15 mL). The basic aqueous layer was cooled in an ice bath and acidified with 1M aqueous HCl solution to pH 2. The acidic aqueous layer was extracted with isopropanol/chloroform (1/1, 3×20 mL). The combined organic extracts were washed with brine, dried over Na2SO4 and filtered. Concentration of the filtrate under reduced pressure afforded 413 mg of 2-methanesulfonyl-2-methyl-propionic acid. The compound did not ionise under LCMS conditions, thus the structure was confirmed by 1H-NMR spectroscopy:

Workup

  1. washwashed with DCM (2×15 mL)
  2. temperatureThe basic aqueous layer was cooled in an ice bath
  3. extractionThe acidic aqueous layer was extracted with isopropanol/chloroform (1/1, 3×20 mL)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered

Sources & evidence

ORD record
ord-f2a150604a4d4552b54944e02fdf185a
Source dataset
uspto-grants-2014_09
Patent number
US08829034B2

Reaction notes

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