[F:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][CH2:7][C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14]C)=[O:13])=[CH:10][C:9]=2[C:18]([O:20][CH3:21])=[O:19])=[CH:4][CH:3]=1.O1CCOCC1.CO.[OH-].[Na+]>O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH2:7][C:8]2[CH:17]=[CH:16][C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9]=2[C:18]([O:20][CH3:21])=[O:19])=[CH:22][CH:23]=1
A mixture of methyl 4-(4-fluorophenethyl)-3-methoxycarbonylbenzoate (51.00 g., 161.22 mmol), dioxane (650 ml), methanol (650 ml), sodium hydroxide (7.10 g., 177.35 mmol) and water (100 ml) was stirred at ambient temperature under an inert atmosphere for 16 hours. The reaction was evaporated to dryness, water (500 ml) was added to the residue and the mixture extracted with diethyl ether. The organic extracts were dried and evaporated to dryness to give recovered methyl 4-(4-fluorophenethyl)-3-methoxycarbonylbenzoate (7 g). The aqueous layer was acidified to pH 2 with 2M HCl (300 ml) and extracted with ethyl acetate (300 ml). The organic extracts were dried, filtered and evaporated to dryness to give as a white solid 4-(4-fluorophenethyl)-3-methoxycarbonylbenzoic acid (42.00 g).
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