Hydrogen Peroxide → 9H-carbazole-9-hexanol

Participants

Reaction Steps

200 ml of a solution of 9-borabicyclo[3.3.1]-nonane (9-BBN) in tetrahydrofuran (0.5 mol/l) were initially taken in a thoroughly heated 500 ml three-necked flask. After the dropwise addition of a solution of 100 mmol of N-5-hexenylcarbazole in 100 ml of dry tetrahydrofuran, the mixture was stirred for 3 hours at room temperature, after which 60 ml of ethanol, 20 ml of 6N sodium hydroxide solution and 40 ml of hydrogen peroxide (30% strength) were added in succession. Refluxing was carried out for 1 hour, after which the reaction mixture was worked up by adding 200 ml of water and then stripping off the tetrahydrofuran. The resulting N-(6-hydroxyhexyl)-carbazole was extracted with ether, the ether extract was dried and the ether was evaporated. The resulting crude product was then recrystallized from 9:1 hexane/acetone. The pure N-(6-hydroxyhexyl)carbazole obtained in 61% yield was in the form of white crystals.

Provenance & Evidence