Water → HCID 2890476, compound

HRID 2247862Notes

Reaction equation

HRID 2247862 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[OH-].[Na+].[CH3:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][C:14]=1[N+:21]([O-:23])=[O:22].O>C(O)C>[CH3:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[CH:2][C:1]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[O:3])=[CH:15][C:14]=1[N+:21]([O-:23])=[O:22]

Participants

6

Reactant 4

HCID 962WaterHCID 7410AcetophenoneHCID 14798Sodium HydroxideHCID 17989983-Nitro-p-tolualdehyde

Product 1

HCID 2890476HCID 2890476, compoundYield 85.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of acetophenone (7.4 g) and 4N-sodium hydroxide solution (16 ml) in ethanol {60 ml) was added 4-methyl-3-nitrobenzaldehyde (7.4 g) at ambient temperature under stirring and the resultant mixture was stirred at same condition for 1.5 hours. To the reaction mixture was added water and resulting precipitate was collected by filtration. The precipitate was dissolved in a mixture of ethyl acetate and tetrahydrofuran. The solution was washed with brine and dried over magnesium sulfate. The solvent was concentrated in vacuo and the crystalline residue was collected by filtration to give 3-(4-methyl-3-nitrophenyl)-1-phenyl-2-propen-1-one (10.25 g).

Workup

  1. customresulting precipitate
  2. filtrationwas collected by filtration
  3. dissolutionThe precipitate was dissolved in a mixture of ethyl acetate and tetrahydrofuran
  4. washThe solution was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationThe solvent was concentrated in vacuo
  7. filtrationthe crystalline residue was collected by filtration

Sources & evidence

ORD record
ord-f040d0335c0742a6a77d233ff016ba4d
Source dataset
uspto-grants-1991_08
Patent number
US05037824

Reaction notes

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