Reaction #53292

Reaction equation

HCl

Ethyl 4-(4-(2,5-Difluorobenzyloxy)phenyl)-4-oxobutyrate

Ethyl 4-(4-(2,5-difluorobenzyloxy)phenyl)-4-oxobutyrate

NaOH

→

title compound

4-(4-(2,5-Difluorobenzyloxy)phenyl)-4-oxobutyric acid

Solvents

ethanol

Conditions

Workup

1. 1
   Concentrationconcentrated in vacuo
2. 2
   Washwashed with water
3. 3
   WashThe aqueous layer was washed one more time with chloroform
4. 4
   DryingThe combined organic layers were dried over Na2SO4
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated
7. 7
   OtherThe purification

Procedure

To a solution of Ethyl 4-(4-(2,5-Difluorobenzyloxy)phenyl)-4-oxobutyrate (Step B, 16.51 g, 47.4 mmol) in abs ethanol (100 ml) was added 1N NaOH (40 ml) at room temperature. The reaction mixture was stirred for 3 hours, acidified with 1M HCl and concentrated in vacuo. The crude mixture was taken in chloroform and washed with water. The aqueous layer was washed one more time with chloroform. The combined organic layers were dried over Na2SO4, filtered and concentrated. The purification was done by flash. chromatography on silica gel column (chloroform:methanol, 95:5 spiked with acetic acid) to provide the title compound as a white solid.

Source