Acetophenone → 5724-55-0

HRID 2373094Notes

Reaction equation

HRID 2373094 reaction equation
C([C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH:5]=[O:6])#N.C(C1C=CC=CC=1)(=O)C.[OH-].[Na+].[C:22]([C:24]1[CH:29]=[CH:28][C:27]([CH:30](C2C=CC=CC=2)[C:31](=O)C)=[CH:26][CH:25]=1)#[N:23].OS([O-])(=O)=O.[K+]>C(O)C>[CH:9]1[CH:8]=[CH:7][C:4]([C:5](/[CH:31]=[CH:30]/[C:27]2[CH:26]=[CH:25][C:24]([C:22]#[N:23])=[CH:29][CH:28]=2)=[O:6])=[CH:3][CH:10]=1

Participants

7

Reactant 5

HCID 7410AcetophenoneHCID 14798Sodium HydroxideHCID 1012092-CyanobenzaldehydeHCID 516920Potassium bisulfateHCID 54423443HCID 54423443, compound

Product 1

HCID 53671615724-55-0

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1 Mol of cyanobenzaldehyde is reacted with 1 mol of acetophenone and sodium hydroxide in ethanol. The resulting 3-(p-cyanophenyl)-3-phenylpropanone is reacted with KHSO4 to obtain p-cyanochalcone. The p-cyanochalcone is hydrogenated in the presence of a platinum catalyst to produce 3-(p-cyanophenyl)-1-phenylpropanone. The resulting compound is reacted with hydrazine and potassium hydroxide in triethylene glycol to produce p-cyanodiphenylpropane. The p-cyanodiphenylpropane is reacted with fuming nitric acid and acetic acid anhydride to produce 1-(p-cyanophenyl)-3-(p-nitrophenyl)-propane.

Sources & evidence

ORD record
ord-11cad1fb400f4dff84d70cc150eefec4
Source dataset
uspto-grants-1992_03
Patent number
US05101411

Reaction notes

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