[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[C:4]([CH:12]([CH3:14])[CH3:13])[CH:3]=1.O.[OH-].[Li+].O1CCOCC1.Cl>O>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([OH:8])=[O:7])=[C:4]([CH:12]([CH3:14])[CH3:13])[CH:3]=1A mixture of methyl 4-bromo-2-isopropylbenzoate (0.41 g) and lithium hydroxide monohydrate (0.67 g) in water (1 mL)/1,4-dioxane (3 mL) was stirred at room temperature for 5 days. 2 mol/L hydrochloric acid (10 mL) was added to the mixture, and the resulting mixture was extracted with ethyl acetate. The solvent was evaporated under reduced pressure, and the residue was recrystallized from ethyl acetate/n-hexane to afford the title compound (0.276 g).
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