9-ethyl-9H-carbazole-3-carbaldehyde → 9-Ethyl-9H-carbazole-3-carboxylic acid

Participants

Reaction Steps

To a solution of 9-Ethyl-9H-carbazole-3-carbaldehyde (Aldrich, 5.0 g, 22.39 mmol) in acetone (100 ml) at 70° C. under nitrogen was added dropwise a solution of KMnO4 (4.74 g, 30.00 mmol) in H2O (100 ml) slowly over 1 hour. When the reaction was complete the reaction mixture was filtered through celite, the celite pad washed with H2O/acetone, and the filtrate washed with ether. The aqueous layer was then acidified to pH 2 with aqueous HCl, and the white precipitate filtered and dried under vacuum to afford the desired product (4.05 g, 76% yield). MS m/z @ 240 (m+1).

Provenance & Evidence