Sodium Hydroxide → 2-(6-Fluoro-1-hydroxy-1-indanyl)acetic acid

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Reaction Steps

A mixture of ethyl 2-(6-fluoro-1-hydroxy-1-indanyl)acetate (44.0 g, 0.18 mol), 1N sodium hydroxide (180 mL) and absolute ethanol (280 mL) was stirred for 18 h at room temperature. The mixture was concentrated in vacuo, diluted with H2O and extracted with diethyl ether. The aqueous phase was acidified (pH 3) with dilute hydrochloric acid and extracted with diethyl ether. The diethyl ether layer was washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo to give 2-(6-fluoro-1-hydroxy-1-indanyl)acetic acid as an amber oil (37.7 g, 100%; Note: This compound spontaneously dehydrated upon standing at room temperature to a mixture of olefins unless immediately reacted with trifluoroacetic acid); NMR (DMSO-d6): d 11.60 (br s, 1H, COOH), 6.75-7.05 (m, 3H, Ar), 5.20 (br s, 1H, OH), 2.22-2.69, 1.77-1.95 (2m's, 6H, 3XCH2).

Provenance & Evidence