Sodium Hydroxide → 2-(3-(4-(Trifluoromethyl)benzyloxy)phenyl)acetic acid
Reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:22]=[CH:21][C:6]([CH2:7][O:8][C:9]2[CH:10]=[C:11]([CH2:15][C:16]([O:18]CC)=[O:17])[CH:12]=[CH:13][CH:14]=2)=[CH:5][CH:4]=1.[OH-].[Na+]>C(O)C>[F:1][C:2]([F:23])([F:24])[C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C:9]2[CH:10]=[C:11]([CH2:15][C:16]([OH:18])=[O:17])[CH:12]=[CH:13][CH:14]=2)=[CH:21][CH:22]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution Ethyl 2-(3-(4-(trifluoromethyl)benzyloxy)phenyl)acetate (Step A, 6 g, 17.7 mmol) in absolute ethanol (70 ml) was added 1N NaOH (36 ml) at room temperature. The reaction mixture was stirred for 3 hours, or until all the starting material is gone, concentrated and diluted with chloroform and acidified by 1M HCl to bring the pH to 3.5-4. The organic layer was washed with brine, dried over Na2SO4, filtered, concentrated and purified by flash chromatography on a silica gel column (chloroform:methanol, 95:5 spiked with acetic acid) to give the title compound as white solid.