Lithium hydroxide, monohydrate → HCID 59704011, compound

HRID 1809365Notes

Reaction equation

HRID 1809365 reaction equation
C([O:3][C:4](=[O:16])[C:5]([S:8]([CH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1)(=[O:10])=[O:9])([CH3:7])[CH3:6])C.O.[OH-].[Li+]>O1CCOCC1.O.O>[CH:11]1([S:8]([C:5]([CH3:7])([CH3:6])[C:4]([OH:16])=[O:3])(=[O:10])=[O:9])[CH2:12][CH2:13][CH2:14][CH2:15]1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59703988HCID 59703988, compound

Product 1

HCID 59704011HCID 59704011, compoundYield 92%

Reagents, catalysts & solvents 2

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

Procedure

To a solution of 5.4 g (21.7 mmol) of 2-cyclopentanesulfonyl-2-methyl-propionic acid ethyl ester in THF/water (4/1, 60 mL) are added 2.3 g (56.6 mmol) of lithium hydroxide monohydrate. The reaction is stirred at room temperature for 18 h. The reaction is further diluted with water (20 mL) and then washed with DCM (2×15 mL). The basic aqueous layer is cooled in an ice bath and then acidified with 2M aqueous HCl solution to pH 2. The acidic aqueous layer is extracted with 2-propanol/chloroform (1/4, 100 mL). The combined organic extracts are washed with brine, dried over Na2SO4 and filtered. Concentration of the filtrate under reduced pressure affords 4.34 g of 2-cyclopentanesulfonyl-2-methyl-propionic acid. Yield: 92%, ES-MS: m/z 221 [M+H]

Workup

  1. washwashed with DCM (2×15 mL)
  2. temperatureThe basic aqueous layer is cooled in an ice bath
  3. extractionThe acidic aqueous layer is extracted with 2-propanol/chloroform (1/4, 100 mL)
  4. washThe combined organic extracts are washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered

Sources & evidence

ORD record
ord-ccda21818917427fa90d4a36d9c765f5
Source dataset
uspto-grants-2013_01
Patent number
US08362039B2

Reaction notes

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