Lithium hydroxide, monohydrate → HCID 67325185, compound

HRID 628774Notes

Reaction equation

HRID 628774 reaction equation
C([O:3][C:4](=[O:21])[C:5]([S:8]([C:11]1[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][CH:12]=1)(=[O:10])=[O:9])([CH3:7])[CH3:6])C.O.[OH-].[Li+]>O1CCOCC1.O.O>[CH3:20][S:17]([C:14]1[CH:15]=[CH:16][C:11]([S:8]([C:5]([CH3:7])([CH3:6])[C:4]([OH:21])=[O:3])(=[O:9])=[O:10])=[CH:12][CH:13]=1)(=[O:19])=[O:18]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67324129HCID 67324129, compound

Product 1

HCID 67325185HCID 67325185, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

To a solution of 0.67 g (2.07 mmol) of 2-(4-methanesulfonyl-benzenesulfonyl)-2-methyl-propionic acid ethyl ester in THF/water (4/1, 10 mL) were added 100 mg (4.14 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 461 mg of 2-(4-methanesulfonyl-benzenesulfonyl)-2-methyl-propionic acid. (73% yield) 1H NMR (400 MHz, DMSO-d6) ppm 1.51 (6H, s), 3.35 (3H, s), 8.08 (2H, d, J=22 Hz), 8.20 (2H, d, J=21 Hz), 13.64 (1H, s)

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-4c0754f607be4430af2fcb9fe4ce091e
Source dataset
uspto-grants-2016_04
Patent number
US09315454B2

Reaction notes

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