1,2-Dichloroethane → HCID 22920215, compound

HRID 1377229Notes

Reaction equation

HRID 1377229 reaction equation
[N+:1]([C:4]1[CH:43]=[CH:42][C:7]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH:17]([CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[CH2:18][C:19]3[CH:24]=[CH:23][C:22]([C:25](=O)[C:26]4[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=4)=[CH:21][CH:20]=3)=[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:11]=[CH:12][C:13]([CH2:16][CH:17]([CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[CH2:18][C:19]3[CH:24]=[CH:23][C:22]([CH2:25][C:26]4[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=4)=[CH:21][CH:20]=3)=[CH:14][CH:15]=2)=[CH:42][CH:43]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 12052TriethylsilaneHCID 22919093HCID 22919093, compound

Product 1

HCID 22920215HCID 22920215, compoundYield 106.1%

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, 40.5 g of 1,3-bis(4-(4-nitrobenzoyl)phenyl)-2-n-hexyl propane, 100 milliliters of 1,2-dichloroethane and 49.7 g of boron trifluoride diethyl ether complex were introduced and heated at reflux. 36.2 g of triethylsilane was added dropwise for 20 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. After washing with an aqueous solution of sodium hydrogencarbonate and water, the solution was dried with anhydrous sodium sulfate. After removing off the solvent by a rotary evaporator, the residue was dissolved in toluene, and a separating operation was carried out by a column chromatography with silica gel. After removing off the solvent again, 40.9 g of 1,3-bis(4-(4-nitrobenzyl)phenyl)-2-n-hexyl propane was obtained as yellow 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. washAfter washing with an aqueous solution of sodium hydrogencarbonate and water
  7. dry with materialthe solution was dried with anhydrous sodium sulfate
  8. customAfter removing off the solvent
  9. customby a rotary evaporator
  10. dissolutionthe residue was dissolved in toluene
  11. customAfter removing off the solvent again

Sources & evidence

ORD record
ord-20a9168df9d34c4db0f241571953e4ec
Source dataset
uspto-grants-1997_09
Patent number
US05663440

Reaction notes

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