3-Phenylprop-2-Enal → 1-(3-Nitrophenyl)-5-phenylpenta-2,4-dien-1-one

HRID 1285279Notes

Reaction equation

HRID 1285279 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[CH:5]=1)=[O:3].[CH:13](=O)[CH:14]=[CH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[OH-].[Na+]>C(O)C>[N+:10]([C:6]1[CH:5]=[C:4]([C:2](=[O:3])[CH:1]=[CH:13][CH:14]=[CH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:9]=[CH:8][CH:7]=1)([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 3073-Phenylprop-2-EnalHCID 8494m-NitroacetophenoneHCID 14798Sodium Hydroxide

Product 1

HCID 537498611-(3-Nitrophenyl)-5-phenylpenta-2,4-dien-1-oneYield 71%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Using a procedure similar to that described in Example D, 33 g of 3-nitroacetophenone and 26.2 g of cinnamaldehyde in 200 ml of ethanol were condensed in the presence of 10 ml of a 5% strength NaOH solution to give 38 g (71% of theory) of 1-(3-nitrophenyl)-5-phenyl-2,4-pentadien-1-one of melting point 127°-129° C.

Sources & evidence

ORD record
ord-9af4327f39064e63a2e4404c8643b10b
Source dataset
uspto-grants-1986_01
Patent number
US04566900

Reaction notes

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