Sodium Hydroxide → 4-[3-(1H-imidazol-1-yl)-2-[[(4-methoxyphenyl)methoxy]methyl]-1E-propenyl]benzoic acid

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Reaction Steps

A solution containing ethyl 4-[3-(1H-imidazol-1-yl)-2-[[(4-methoxyphenyl)methoxy]methyl]-1E-propenyl]benzoate (prepared as in Example 1; 0.7 g, 0.0017 mol) in ethanol (10 ml) was treated with aqueous sodium hydroxide (3.5 ml of 1M). The resulting mixture was stirred at room temperature for 5 hours after which time the solvent was evaporated off under reduced pressure and the resulting residue was dissolved in water (100 ml) and washed with ethyl acetate. The aqueous solution was acidified to pH 6.5 with hydrochloric acid and extracted with ethyl acetate (3×150 ml). The extracts were combined, dried over sodium sulfate, and the solvent was evaporated off under reduced pressure to yield a crude product. The crude product was recrystallised from dichloromethane-pentane to yield 4-[3-(1H-imidazol-1-yl)-2-[[(4-methoxyphenyl)methoxy]methyl]-1E-propenyl]benzoic acid as a colourless, crystalline solid, having a melting point of 120°-122° C. and the following structural characteristics:

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