Iodoethane → 3-Ethoxy-5-nitro-4-phenylbenzoic acid

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Reaction Steps

To a solution of sodium ethanolate (prepared from 0.5 g of sodium) in dry ethanol (40 ml), ethyl 3-hydroxy-5-nitro-4-phenylbenzoate (4.4 g) is added followed by ethyl iodide (2.5 ml), and the resulting solution is refluxed for 20 hours. After about 6 hours an additional amount of sodium ethanolate (prepared from 0.25 g of sodiumn) in dry ethanol (10 ml) is added followed by ethyl iodide (1.3 ml). The mixture is evaporated in vacuo, 2 N sodium hydroxide (25 ml) is added to the residue, and the mixture is heated on a steam bath for 30 minutes to form a clear solution. On cooling, sodium 3-ethoxy-5-nitro-4-phenylbenzoate separates. It is collected by filtration, and washed with a small amount of icecold water. After drying, the sodium salt is dissolved in hot water (50 ml), and the 3-ethoxy-5-nitro-4-phenylbenzoic acid is precipitated by addition of 4 N hydrochloric acid (5 ml). After cooling, the acid is collected by filtration, washed with water and dried. After recrystallization from aqueous ethanol, it is obtained with a melting point of 174°-176° C.

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