Reaction #2006419

Reaction equation

HCl

methyl ester

Methyl-4-(3-oxo-3-phenylpropyl)-benzoate

LiOH

→

title compound

4-(3-oxo-3-Phenylpropyl)-benzoic Acid

Solvents

water THF

Conditions

Workup

1. 1
   Extractionthe solution was extracted with EtOAc
2. 2
   Dryingthe organic layer was dried over anhydrous MgSO4
3. 3
   FiltrationFiltration and evaporation of the solvent under vacuum
4. 4
   Otherfollowed by purification by column chromatography

Procedure

To a solution of methyl ester 47 (195 mg, 0.73 mmol) in water/THF (1:1, 0.07M) was added LiOH (46 mg, 1.1 mmol). The resulting solution was stirred overnight at room temperature or until no starting material was detected by TLC. HCl 1N was added and the solution was extracted with EtOAc and the organic layer was dried over anhydrous MgSO4. Filtration and evaporation of the solvent under vacuum followed by purification by column chromatography using 10% MeOH/CH2Cl2, gave the title compound.

Source