Ethanol → (1H-Indol-5-yl)acetic acid

Participants

Reaction Steps

A solution of 1-(4-methylphenylsufonyl)indole-6-acetonitrile (9.5 g) in ethanol (58 ml) was treated with 20% (w/v) sodium hydroxide (58 ml) and heated to reflux for 2.5 hr. The ethanol was evaporated and the aqueous residue was slowly acidified at 0° with concentrated hydrochloric acid. The white precipitate was collected by filtration, washed with water and dried under vacuum to give indole-5-acetic acid (4.1 g, 68%) as an ivory powder: NMR (250 MHz, DMSO-d6): 3.57(s, 2H, ArCH2), 9.65(dd, 1H, H6 -indole), 7.40(s, 1H, H4 -indole).

Provenance & Evidence