4-Nitrobenzoyl chloride → HCID 22919097, compound

HRID 1377225Notes

Reaction equation

HRID 1377225 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:13]1([CH:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>ClCCCl.[Fe](Cl)Cl>[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([C:16]2[CH:17]=[CH:18][C:13]([CH:19]([C:26]3[CH:27]=[CH:28][C:29]([C:8](=[O:9])[C:7]4[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=4)=[CH:30][CH:31]=3)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:14][CH:15]=2)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 85024-Nitrobenzoyl chlorideHCID 2713351,1,-Diphenylheptane

Product 1

HCID 22919097HCID 22919097, compoundYield 73.3%

Reagents, catalysts & solvents 2

HCID 24458Ferrous ChlorideCatalystHCID 111,2-DichloroethaneSolvent2×

Procedure

In a 200-milliliter three-necked flask equipped with a stirring device, a thermometer and a nitrogen substituting device, 17.4 g of iron chloride, 16.7 g of paranitrobenzoyl chloride and 40 milliliters of 1,2-dichloroethane were introduced. Then, a solution of 9.0 g of 1,1-diphenyl heptane in 10 milliliters of 1,2-dichloroethane was added dropwise for 15 minutes with an ice bath. Thereafter, the solution was stirred for 3 hours and 40 minutes with heating to a reflux temperature. After the end of the reaction was confirmed by a liquid chromatography, the solution was poured in ice water containing dilute hydrochloric acid, and then extracted with chloroform. The solution was washed with hydrochloric acid, an aqueous solution of sodium hydroxide and water, and then dried with anhydrous sodium sulfate. After removing off the solvent by a rotary evaporator, the solution was dissolved in chloroform and subjected to a separating operation by a column chromatography with silica gel, to obtain 14.4 g of 1,1-bis(4-(4-nitrobenzoyl)phenyl)heptane as red oil.

Workup

  1. customIn a 200-milliliter three-necked flask equipped with a stirring device
  2. temperaturewith heating to a reflux temperature
  3. extractionextracted with chloroform
  4. washThe solution was washed with hydrochloric acid
  5. dry with materialan aqueous solution of sodium hydroxide and water, and then dried with anhydrous sodium sulfate
  6. customAfter removing off the solvent
  7. customby a rotary evaporator
  8. dissolutionthe solution was dissolved in chloroform

Sources & evidence

ORD record
ord-f27e95d1bf4a4386a7d90e351b50a965
Source dataset
uspto-grants-1997_09
Patent number
US05663440

Reaction notes

Loading…