Sodium Carbonate → HCID 22919105, compound

HRID 1377218Notes

Reaction equation

HRID 1377218 reaction equation
[N+:1]([C:4]1[CH:36]=[CH:35][C:7]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([C:24](=O)[C:25]4[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=4)=[CH:20][CH:19]=3)=[CH:12][CH:11]=2)=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].FC(F)(F)S(O)(=O)=O.C([SiH](CC)CC)C.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][C:10]2[CH:11]=[CH:12][C:13]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([CH2:24][C:25]4[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=4)=[CH:20][CH:19]=3)=[CH:14][CH:15]=2)=[CH:35][CH:36]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 12052TriethylsilaneHCID 62406Trifluoromethanesulfonic acidHCID 22920243HCID 22920243, compound

Product 1

HCID 22919105HCID 22919105, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In a 1-liter three-necked flask equipped with a stirring device, a thermometer and a nitrogen substituting device, 32.6 g of 1,2-bis(4-(4-nitrobenzoyl)phenyl)ethane and 200 milliliters of dichloromethane were introduced. 42.0 g of trifluoromethane sulfonic acid was added dropwise for 15 minutes. Subsequently, a solution of 40.7 g of triethylsilane in 50 milliliters of dichloromethane was added dropwise for 1 hour. After the end of the dropwise addition, stirring was carried out for 18 hours with warming to room temperature. After the end of the reaction was confirmed by a liquid chromatography, the reaction solution was neutralized with an aqueous solution of sodium carbonate and washed with water. After removing dichloromethane by a rotary evaporator, 27.6 g of 1,2-bis(4-(4-nitrobenzyl)phenyl)ethane was obtained as crystals by recrystallizing from a toluene solvent.

Workup

  1. customIn a 1-liter three-necked flask equipped with a stirring device
  2. additionAfter the end of the dropwise addition
  3. washwashed with water
  4. customAfter removing dichloromethane
  5. customby a rotary evaporator

Sources & evidence

ORD record
ord-c09c5530a4ff48e18063d6e4ec734eec
Source dataset
uspto-grants-1997_09
Patent number
US05663440

Reaction notes

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