Sodium Hydroxide → 2-(4-Chloro-6-fluoro-1-hydroxy-1-indanyl)acetic acid
Reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2([CH2:13][C:14]([O:16]CC)=[O:15])[OH:12].[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2([CH2:13][C:14]([OH:16])=[O:15])[OH:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of ethyl 2-(4-chloro-6-fluoro-1-hydroxy-1-indanyl)acetate (14.5 g, 0.05 mol), 1N sodium hydroxide (52 ml) and absolute ethanol (100 ml) was stirred for 18 h at room temperature. The mixture was concentrated in vacuo, diluted with H2O and washed with diethyl ether. The aqueous phase was neutralised with 1.0N hydrochloric acid (52 ml) and extracted with diethyl ether. The diethyl ether extracts were dried over sodium sulphate, filtered and concentrated in vacuo to give 12.5 g (96%) of crude 2-(4-chloro-6-fluoro-1-hydroxy-1-indanyl)acetic acid. This material was used immediately without further purification.