1,2-Dichloroethane → HCID 22920110, compound

HRID 1377226Notes

Reaction equation

HRID 1377226 reaction equation
[N+:1]([C:4]1[CH:41]=[CH:40][C:7]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([CH:16]([C:23]3[CH:28]=[CH:27][C:26]([C:29](=O)[C:30]4[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][CH:31]=4)=[CH:25][CH:24]=3)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:12][CH:11]=2)=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].ClCCCl.C([SiH](CC)CC)C>O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][C:10]2[CH:15]=[CH:14][C:13]([CH:16]([C:23]3[CH:28]=[CH:27][C:26]([CH2:29][C:30]4[CH:31]=[CH:32][C:33]([N+:36]([O-:38])=[O:37])=[CH:34][CH:35]=4)=[CH:25][CH:24]=3)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:12][CH:11]=2)=[CH:40][CH:41]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 12052TriethylsilaneHCID 22919097HCID 22919097, compound

Product 1

HCID 22920110HCID 22920110, compoundYield 103%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 1-liter three-necked flask equipped with a stirring device, a thermometer and a nitrogen substituting device, 14.4 g of 1,1-bis(4-(4-nitrobenzoyl)phenyl)heptane, 60 milliliters of 1,2-dichloroethane and 19.4 g of boron trifluoride diethyl ether complex were introduced and heated at reflux. 14.4 g of triethylsilane was added dropwise for 15 minutes with maintaining the temperature. After the end of the reaction was confirmed by a liquid chromatography, the reaction solution was poured in water and extracted with chloroform. The solution was washed with an aqueous solution of sodium hydrogencarbonate and water, and then dried with anhydrous sodium sulfate. After removing off the solvent by a rotary evaporator, the solution was dissolved in toluene and subjected to a separating operation by a column chromatography with silica gel. After removing off the solvent again, 14.08 g of 1,1-bis(4-(4-nitrobenzyl)phenyl) heptane was obtained as red oil.

Workup

  1. customIn a 1-liter three-necked flask equipped with a stirring device
  2. temperatureheated
  3. temperatureat reflux
  4. temperaturewith maintaining the temperature
  5. extractionextracted with chloroform
  6. washThe solution was washed with an aqueous solution of sodium hydrogencarbonate and water
  7. dry with materialdried with anhydrous sodium sulfate
  8. customAfter removing off the solvent
  9. customby a rotary evaporator
  10. dissolutionthe solution was dissolved in toluene
  11. customAfter removing off the solvent again

Sources & evidence

ORD record
ord-6329e99673ac44f59ac605771c10a9b2
Source dataset
uspto-grants-1997_09
Patent number
US05663440

Reaction notes

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