N-ethyl carbazole → Octanal

HRID 457458Notes

Reaction equation

HRID 457458 reaction equation
C(N1C2C=CC=CC=2C2C1=CC=CC=2)C.C(Cl)(=O)C1C=CC=CC=1.[Al+3].[Cl-].[Cl-].[Cl-].[C:29](Cl)(=[O:37])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]>C(Cl)Cl>[CH:29](=[O:37])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]

Participants

6

Reactant 4

HCID 6836N-ethyl carbazoleHCID 7412Benzoyl chlorideHCID 8124Octanoyl chlorideHCID 6451240Aluminum(III) Chloride2×

Product 1

HCID 454OctanalYield 234.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 7.83 g (40.1 mmol) of N-ethylcarbazole in 40 mL of CH2Cl2 are added 5.91 g (42.0 mmol) of benzoyl chloride and 5.88 g (44.1 mmol) of AlCl3. After stirring for 4 h at room temperature, 6.89 g (42.3 mmol) of octanoyl chloride and 5.92 g (44.4 mmol) of AlCl3 are added. This reaction mixture is stirred at room temperature for 4.5 h. Then, the reaction mixture is poured into ice-water. The products are extracted with CH2Cl2. The CH2Cl2 layer is washed with water, saturated NaHCO3 aq. solution and with brine, followed by drying over anhydrous MgSO4. Purification by column chromatography on silica gel with CH2Cl2-hexane(1:1) as eluent affords 12.7 g of a white solid (74.2%).

Workup

  1. stirringThis reaction mixture is stirred at room temperature for 4.5 h
  2. extractionThe products are extracted with CH2Cl2
  3. washThe CH2Cl2 layer is washed with water, saturated NaHCO3 aq. solution and with brine
  4. dry with materialby drying over anhydrous MgSO4
  5. customPurification by column chromatography on silica gel with CH2Cl2-hexane(1:1) as eluent

Sources & evidence

ORD record
ord-d90ec6bcbb52409eb7cedf3a167b7cba
Source dataset
uspto-grants-2007_03
Patent number
US07189489B2

Reaction notes

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