Hydrogen Peroxide → 9H-carbazole-9-hexanol

Participants

Reaction Steps

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

Provenance & Evidence