4-Nitrobenzoyl chloride → 1,6-Bis(4-(4-nitrobenzoyl)phenyl)hexane

HRID 1377222Notes

Reaction equation

HRID 1377222 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[N+:5]([C:8]1[CH:16]=[CH:15][C:11]([C:12](Cl)=[O:13])=[CH:10][CH:9]=1)([O-:7])=[O:6].[C:17]1([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>ClCCCl>[N+:5]([C:8]1[CH:16]=[CH:15][C:11]([C:12]([C:20]2[CH:21]=[CH:22][C:17]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]3[CH:30]=[CH:31][C:32]([C:12](=[O:13])[C:11]4[CH:10]=[CH:9][C:8]([N+:5]([O-:7])=[O:6])=[CH:16][CH:15]=4)=[CH:33][CH:34]=3)=[CH:18][CH:19]=2)=[O:13])=[CH:10][CH:9]=1)([O-:7])=[O:6]

Participants

5

Reactant 3

HCID 85024-Nitrobenzoyl chlorideHCID 1368531,6-DiphenylhexaneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 229197341,6-Bis(4-(4-nitrobenzoyl)phenyl)hexaneYield 105.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

In a 1-liter three-necked flask equipped with a stirring device, a thermometer and a nitrogen substituting device, 33.3 g of aluminum chloride and 200 milliliters of 1,2-dichloroethane were mixed and then 40.8 g of paranitrobenzoyl chloride was introduced with ice cooling to be dissolved. Then, a solution of 23.6 g of 1,6-diphenylhexane in 50 milliliters of 1,2-dichloroethane was added dropwise for 30 minutes. After the end of the dropwise adding, the solution was stirred for 3 hours with warming back to the room temperature. After the end of reaction was confirmed by a liquid chromatography, the reaction solution was poured in 500 milliliters of ice water, and then extracted with 1.8 liters of chloroform. The solution was washed with an aqueous solution of sodium hydrogencarbonate and water, and then dried with magnesium sulfate. Chloroform was removed off by a rotary evaporator, and then 56.0 g of 1,6-bis(4-(4-nitrobenzoyl)phenyl)hexane was obtained as crystals by recrystallizing from a mixed solvent of chloroform and ethyl acetate.

Workup

  1. customIn a 1-liter three-necked flask equipped with a stirring device
  2. dissolutionto be dissolved
  3. additionAfter the end of the dropwise adding
  4. customAfter the end of reaction
  5. extractionextracted with 1.8 liters of chloroform
  6. washThe solution was washed with an aqueous solution of sodium hydrogencarbonate and water
  7. dry with materialdried with magnesium sulfate
  8. customChloroform was removed off by a rotary evaporator

Sources & evidence

ORD record
ord-73af899bcee94287bef83bf5a7fa3cb3
Source dataset
uspto-grants-1997_09
Patent number
US05663440

Reaction notes

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