HCID 15123923, compound → HCID 54296116, compound

HRID 1377232Notes

Reaction equation

HRID 1377232 reaction equation
[N+:1]([C:4]1[CH:35]=[CH:34][C:7]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([C:23](=O)[C:24]4[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[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]>O1CCCC1>[N+:1]([C:4]1[CH:35]=[CH:34][C:7]([C:8](=[C:10]2[CH:15]=[CH:14][C:13]([CH2:16][C:17]3[CH:22]=[CH:21][C:20](=[C:23]([C:24]4[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=4)[CH2:6][CH2:7][CH3:8])[CH2:19][CH:18]=3)=[CH:12][CH2:11]2)[CH2:5][CH2:4][CH3:35])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

3

Reactant 1

HCID 15123923HCID 15123923, compound

Product 1

HCID 54296116HCID 54296116, compoundYield 102.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Then, a solution of 30.0 g (0.064 mole) of 1,1-bis(4-(4-nitrobenzoyl)phenyl)methane in 1 liter of tetrahydrofuran was added dropwise for 1 hour, and stirred for 8 hours with maintaining at 3° to 5° C. At that time, hue was changed to dark purple. After the end of the reaction was confirmed by a liquid chromatography, the solution was poured in 400 milliliters of ice water, and extracted with 800 milliliters of chloroform after adding 400 milliliters of a 4N-HCl aqueous solution. Thereafter, the solution was washed with a 6N-HCl aqueous solution, an aqueous solution of sodium hydrogencarbonate, brine and water, and then removed off chloroform by a rotary evaporator. The residue was dissolved in toluene and treated with a silica gel (800 g) column, to obtain 17.1 g of 1,1-bis(4-(1-(4-nitrophenyl)butylidene)phenyl)methane as highly viscous oil.

Workup

  1. temperaturewith maintaining at 3° to 5° C
  2. extractionextracted with 800 milliliters of chloroform
  3. additionafter adding 400 milliliters of a 4N-HCl aqueous solution
  4. washThereafter, the solution was washed with a 6N-HCl aqueous solution
  5. customan aqueous solution of sodium hydrogencarbonate, brine and water, and then removed off chloroform
  6. customby a rotary evaporator
  7. dissolutionThe residue was dissolved in toluene
  8. additiontreated with a silica gel (800 g) column

Sources & evidence

ORD record
ord-7f4e28843c9f466a83ec31007f824e80
Source dataset
uspto-grants-1997_09
Patent number
US05663440

Reaction notes

Loading…