Butyryl chloride → Propionyl chloride

HRID 742511Notes

Reaction equation

HRID 742511 reaction equation
[C:1]([Cl:6])(=[O:5])[CH2:2][CH2:3]C.[Al+3].[Cl-].[Cl-].[Cl-].[CH2:11]([N:15]1[C:27]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:21]2[C:16]1=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:12][CH2:13][CH3:14]>C(Cl)Cl>[C:1]([Cl:6])(=[O:5])[CH2:2][CH3:3].[CH2:11]([N:15]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=2[C:22]2[C:27]1=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 3

HCID 8855Butyryl chlorideHCID 73872N-ButylcarbazoleHCID 6451240Aluminum(III) Chloride

Product 2

HCID 62324Propionyl chlorideHCID 73872N-Butylcarbazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

46.9 g (0.44 tool) of butyryl chloride are added dropwise to a suspension of 93.3 g (0.7 tool) of AlCl3 in 100 ml of methylene chloride in the course of 30 minutes, while stirring and cooling to -10° to -5°. A solution of 22.3 g (0.1 tool) of N-butylcarbazole in 50 ml of CH2Cl2 is then added dropwise at -10° to -5° in the course of 2 hours. The suspension is stirred at 0° to 20° for 16 hours and then poured onto ice. The emulsion formed is extracted twice with CHCl3 and the extract is washed with water, dried over MgSO4 and evaporated. The crude 3,6-dibutyryl-9-butyl-9H-carbazole is re-crystallized from 80 ml of ethanol. The resulting crystals have a melting point of 107°-109°. 3,6-Dipropionyl-9-butyl-9H-carbazole, which has a melting point of 142°-144° is obtained in an analogous manner from 81.4 g of propionyl chloride and 44.7 g of N-butylcarbazole.

Workup

  1. temperaturecooling to -10° to -5°
  2. stirringThe suspension is stirred at 0° to 20° for 16 hours
  3. additionpoured onto ice
  4. customThe emulsion formed
  5. extractionis extracted twice with CHCl3
  6. washthe extract is washed with water
  7. dry with materialdried over MgSO4
  8. customevaporated
  9. customThe crude 3,6-dibutyryl-9-butyl-9H-carbazole is re-crystallized from 80 ml of ethanol

Sources & evidence

ORD record
ord-0796f443ffa445a982890c15476483f6
Source dataset
uspto-grants-1996_09
Patent number
US05554663

Reaction notes

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