Hydrogen Peroxide → 9H-carbazole-9-hexanol

HRID 2372872Notes

Reaction equation

HRID 2372872 reaction equation
C12BC(CCC1)CCC2.[CH2:10]([N:16]1[C:28]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:22]2[C:17]1=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:11][CH2:12][CH2:13][CH:14]=[CH2:15].[OH-:29].[Na+].OO>O1CCCC1.O.C(O)C>[OH:29][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][N:16]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:22]=2[C:23]2[C:28]1=[CH:27][CH:26]=[CH:25][CH:24]=2

Participants

8

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 15597042HCID 15597042, compound

Product 1

HCID 6402679H-carbazole-9-hexanolYield 60%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

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:

Workup

  1. temperatureThe reaction mixture was then refluxed for one hour

Sources & evidence

ORD record
ord-6f5c28bc94354ee087b0ff5adad6f4f4
Source dataset
uspto-grants-1992_03
Patent number
US05100971

Reaction notes

Loading…