Water → alpha-Benzamido(2,3-dihydro-5-benzofuranyl)acetic acid

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Reaction Steps

2,3-Dihydrobenzofuran (4.8 g, 40 mmole) is stirred with 9.0 g (40 mmole) of α-hydroxyhippuric acid in 200 ml of 10% H2SO4 -acetic acid mixture. The reaction is run at room temperature for 0.5 hour. After the half-hour, the reaction mixture is poured into 500 ml of water. The aqueous solution is extracted with ethyl acetate (4 × 100 ml). The ethyl acetate extracts are dried over magnesium sulfate and then evaporated to give α-benzamido(2,3-dihydro-5-benzofuranyl)acetic acid. Recrystallization of the crude benzamido compound from hexane-methylene chloride gives 11.56 g (94% yield).

Provenance & Evidence