Lithium hydroxide, monohydrate → 2-(4-Iodophenyl)propanoic acid

HRID 330812

Reaction equation

HRID 330812 reaction equation
O.[OH-].[Li+].C[O:5][C:6](=[O:16])[CH:7]([C:9]1[CH:14]=[CH:13][C:12]([I:15])=[CH:11][CH:10]=1)[CH3:8]>O.C1COCC1.CO>[I:15][C:12]1[CH:11]=[CH:10][C:9]([CH:7]([CH3:8])[C:6]([OH:16])=[O:5])=[CH:14][CH:13]=1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 10589545Methyl 2-(4-iodophenyl)propanoate

Product 1

HCID 152255732-(4-Iodophenyl)propanoic acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.610 g (14.6 mmol) lithiumhydroxide monohydrate in 15 mL water are added to 2.12 g (7.31 mmol) 2-(4-iodo-phenyl)-propionic acid methyl ester (Bioorg. Med. Chem. Lett. 2010, 20, 896) in 20 mL THF and 12 mL MeOH at 0° C. Cooling is removed and the mixture is stirred at rt for 2 h. After that time, the mixture is acidified with 1 N HCl to pH˜1 and extracted with DCM. The organic layer is washed with brine, dried over sodium sulphate and the solvent is evaporated. The product is used without further purification in Example IV.1

Workup

  1. temperatureCooling
  2. customis removed
  3. extractionextracted with DCM
  4. washThe organic layer is washed with brine
  5. dry with materialdried over sodium sulphate
  6. customthe solvent is evaporated

Sources & evidence

ORD record
ord-9688652224b341aeb2d3783198eb34d3
Source dataset
uspto-grants-2014_11
Patent number
US08877754B2

Linked notes

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