4-Nitrobenzaldehyde → 1,2-Bis(4-nitrophenyl)ethanone

HRID 2372369Notes

Reaction equation

HRID 2372369 reaction equation
[OH-].[K+].N([CH:10]([C:27]1[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=1)P(OC1C=CC=CC=1)(OC1C=CC=CC=1)=O)C1C=CC=CC=1.[N+:36]([C:39]1[CH:46]=[CH:45][C:42]([CH:43]=[O:44])=[CH:41][CH:40]=1)([O-:38])=[O:37]>CO.C1COCC1>[N+:36]([C:39]1[CH:40]=[CH:41][C:42]([C:43](=[O:44])[CH2:10][C:27]2[CH:28]=[CH:29][C:30]([N+:33]([O-:35])=[O:34])=[CH:31][CH:32]=2)=[CH:45][CH:46]=1)([O-:38])=[O:37]

Participants

6

Reactant 3

HCID 5414-NitrobenzaldehydeHCID 14797Potassium HydroxideHCID 12240723HCID 12240723, compound

Product 1

HCID 122407241,2-Bis(4-nitrophenyl)ethanoneYield 95.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of KOH (7.56 g, 0.13 mol) in MeOH (75 ml) was added to the phosphonate ester 33 (62.1 g, 0.13 mol) in THF (400 ml) at -78° C. for 0.5 hour and p-nitrobenzaldehyde (20.3 g, 0.13 mol) in 200 ml of THF was added over 0.5 hour. The reaction was warmed to room temperature and stirred an additional 2 hours. THF was removed under reduced pressure. The residue was taken up in EtOAc and washed twice with 5% aqueous NaHCO3 and once with brine. The ethyl acetate was removed under reduced pressure. The dark red enemine was dissolved in CH3OH (600 ml) and concentrated HCl (0.2 ml) was added. The solution was stirred for 1 hour at room temperature and diluted with H2O (500 ml). The solid was filtered, washed with ether and dried to afford 34 (35.6 g, 82.0%), m.p. 131°-133° C.

Workup

  1. customTHF was removed under reduced pressure
  2. washwashed twice with 5% aqueous NaHCO3 and once with brine
  3. customThe ethyl acetate was removed under reduced pressure
  4. dissolutionThe dark red enemine was dissolved in CH3OH (600 ml)
  5. additionconcentrated HCl (0.2 ml) was added
  6. stirringThe solution was stirred for 1 hour at room temperature
  7. additiondiluted with H2O (500 ml)
  8. filtrationThe solid was filtered
  9. washwashed with ether
  10. customdried

Sources & evidence

ORD record
ord-ef995545ee344040b997866794cd2f2f
Source dataset
uspto-grants-1992_03
Patent number
US05098918

Reaction notes

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