Sodium Carbonate → 1,4-Bis(4-(4-nitrophenylmethyl)phenylmethyl)benzene

HRID 1377212Notes

Reaction equation

HRID 1377212 reaction equation
[N+:1]([C:4]1[CH:42]=[CH:41][C:7]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([CH2:23][C:24]4[CH:29]=[CH:28][C:27]([C:30](=O)[C:31]5[CH:36]=[CH:35][C:34]([N+:37]([O-:39])=[O:38])=[CH:33][CH:32]=5)=[CH:26][CH:25]=4)=[CH:19][CH:18]=3)=[CH:12][CH:11]=2)=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].C([SiH](CC)CC)C.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[N+:1]([C:4]1[CH:42]=[CH:41][C:7]([CH2:8][C:10]2[CH:11]=[CH:12][C:13]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([CH2:23][C:24]4[CH:29]=[CH:28][C:27]([CH2:30][C:31]5[CH:32]=[CH:33][C:34]([N+:37]([O-:39])=[O:38])=[CH:35][CH:36]=5)=[CH:26][CH:25]=4)=[CH:19][CH:18]=3)=[CH:14][CH:15]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 12052TriethylsilaneHCID 229205171,4-Bis(4-(4-nitrobenzoyl)phenylmethyl)benzene

Product 1

HCID 229198971,4-Bis(4-(4-nitrophenylmethyl)phenylmethyl)benzeneYield 81.1%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent3×

Procedure

In a 3-liter four-necked flask equipped with a stirring device, a thermometer, a condenser and a nitrogen substituting device, 34.39 g of 1,4-bis(4-(4-nitrobenzoyl)phenylmethyl) benzene was dissolved in 1000 milliliters of dichloromethane, and a solution of 37.8 g of titanium tetrachloride in 50 milliliters of dichloromethane was added dropwise for 1 hour with ice cooling. Subsequently, a solution of 41.46 g of triethylsilane in 50 milliliters of dichloromethane was added for 1 hour. 30 minutes after the end of the dropwise addition, stirring was carried out for 7 hours with ice cooling. 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 then washed with water. After removing off dichloromethane by a rotary evaporator, the solution was dissolved in chloroform, treated with an alumina column, and removed off the solvent from the solute. By recrystallizing the concentrate from an ethyl acetate solvent, 26.48 g of 1,4-bis(4-(4-nitrophenylmethyl)phenylmethyl)benzene was obtained as crystals.

Workup

  1. customIn a 3-liter four-necked flask equipped with a stirring device
  2. addition30 minutes after the end of the dropwise addition
  3. washwashed with water
  4. customAfter removing off dichloromethane
  5. customby a rotary evaporator
  6. dissolutionthe solution was dissolved in chloroform
  7. additiontreated with an alumina column
  8. customremoved off the solvent from the solute
  9. customBy recrystallizing the
  10. concentrationconcentrate from an ethyl acetate solvent

Sources & evidence

ORD record
ord-3077d8e7874349cc8e1d03a804e67b99
Source dataset
uspto-grants-1997_09
Patent number
US05663440

Reaction notes

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