Lithium hydroxide, monohydrate → HCID 58656151, compound

HRID 73230Notes

Reaction equation

HRID 73230 reaction equation
C([O:3][C:4](=[O:17])[C:5]([S:8]([CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)(=[O:10])=[O:9])([CH3:7])[CH3:6])C.O.[OH-].[Li+]>C1COCC1.O.O>[CH:11]1([S:8]([C:5]([CH3:7])([CH3:6])[C:4]([OH:17])=[O:3])(=[O:10])=[O:9])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59704012Ethyl 2-(cyclohexylsulfonyl)-2-methylpropanoate

Product 1

HCID 58656151HCID 58656151, compoundYield 95.7%

Reagents, catalysts & solvents 2

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

Procedure

To a solution of 3.47 g (13.2 mmol) of 2-cyclohexanesulfonyl-2-methyl-propionic acid ethyl ester in THF/water (4/1, 50 mL) were added 1.11 g (26.4 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 then acidified with 1M aqueous HCl solution to pH 2. The acidic aqueous layer was extracted with DCM (3×20 mL). The combined organic extracts were washed with brine, dried over Na2SO4 and filtered. Concentration of the filtrate under reduced pressure afforded 2.96 g of 2-cyclohexanesulfonyl-2-methyl-propionic acid.

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 DCM (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-224f84fba2b94cfab3920299c0ab9252
Source dataset
uspto-grants-2014_09
Patent number
US08829034B2

Reaction notes

Loading…