Benzyl Bromide → 3-Benzyloxy-5-nitro-4-phenylbenzoic acid

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Reaction Steps

A mixture of 3-hydroxy-5-nitro-4-phenylbenzoic acid (3.0 g), benzylbromide (1.5 ml) and 1 N sodium hydroxide (30 ml) is stirred at room temperature for 6-7 hours. After cooling, the precipitated sodium 3-benzyloxy-5-nitro-4-phenylbenzoate is collected by filtration and washed with a small amount of icecold water. After drying, the sodium salt is dissolved in hot water (100 ml), and the 3-benzyloxy-5-nitro-4-phenylbenzoic acid is precipitated by addition of 4 N hydrochloric acid (10 ml). After cooling, the acid is collected by filtration, washed with water and dried. After recrystallization twice from isopropanol, it is obtained with a melting point of 188.5°-189.5° C.

Provenance & Evidence