Lithium hydroxide, monohydrate → HCID 58198421, compound

HRID 545316Notes

Reaction equation

HRID 545316 reaction equation
C([O:3][C:4]([C:6]1([S:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH2:8][CH2:7]1)=[O:5])C.O.[OH-].[Li+]>C(O)(C)C.C(Cl)(Cl)Cl>[F:20][C:18]([F:19])([F:21])[C:15]1[CH:14]=[CH:13][C:12]([S:9]([C:6]2([C:4]([OH:5])=[O:3])[CH2:7][CH2:8]2)(=[O:10])=[O:11])=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 58198500HCID 58198500, compound

Product 1

HCID 58198421HCID 58198421, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 21906603Chloroform isopropyl alcoholSolvent

Procedure

To a solution of 2.99 g (9.29 mmol) of 1-(4-trifluoromethyl -benzenesulfonyl)-cyclopropanecarboxylic acid ethyl ester in THF/water (1/1, 50 mL) were added 0.82 g (19.5 mmol) of lithium hydroxide monohydrate. The reaction was stirred at room temperature for 18 h. The organic solvent was removed under reduced pressure and the aqueous layer washed with diethyl ether (2×50 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 ethyl acetate (3×50 mL). The combined organic extracts were washed with brine, dried over Na2SO4 and filtered. Concentration of the filtrate under reduced pressure afforded 2.19 g of 1-(4-trifluoromethyl-benzenesulfonyl)-cyclopropanecarboxylic acid.

Workup

  1. customThe organic solvent was removed under reduced pressure
  2. washthe aqueous layer washed with diethyl ether (2×50 mL)
  3. temperatureThe basic aqueous layer was cooled in an ice bath
  4. extractionThe acidic aqueous layer was extracted with ethyl acetate (3×50 mL)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered

Sources & evidence

ORD record
ord-090b2cceb2634d5f89af9bd10d6f4da6
Source dataset
uspto-grants-2011_05
Patent number
US07935715B2

Reaction notes

Loading…