4-Nitrobenzaldehyde → HCID 54479119, compound

HRID 1285277Notes

Reaction equation

HRID 1285277 reaction equation
[OH-].[Na+].[CH:3](=[CH:12][C:13](=[O:15])[CH3:14])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[N+:16]([C:19]1[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=1)([O-:18])=[O:17]>C(O)C>[N+:16]([C:19]1[CH:26]=[CH:25][C:22]([CH:23]=[CH:14][C:13](=[O:15])[CH:12]=[CH:3][CH:4]=[CH:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[CH:21][CH:20]=1)([O-:18])=[O:17]

Participants

5

Reactant 3

HCID 5414-NitrobenzaldehydeHCID 14798Sodium HydroxideHCID 1075126-Phenylhexa-3,5-dien-2-one

Product 1

HCID 54479119HCID 54479119, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

16.2 g of a 10% strength NaOH solution were added dropwise, while cooling slightly, to a mixture of 46.5 g of cinnamalacetone, 45.4 g of p-nitrobenzaldehyde and 160 ml of ethanol at 25° C. The reaction mixture became clear after a short time, and a yellow solid subsequently separated out. The mixture was stirred for one hour, after which the solid was filtered off under suction, washed with diethyl ether, and dried under reduced pressure to give 76 g (91% of theory) of 1-(4-nitrophenyl)-7-phenyl-1,4,6-heptatrien-3-one of melting point 168°-170° C.

Workup

  1. customa yellow solid subsequently separated out
  2. filtrationafter which the solid was filtered off under suction
  3. washwashed with diethyl ether
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-ad3c9be6255f4864a55749906fe1283b
Source dataset
uspto-grants-1986_01
Patent number
US04566900

Reaction notes

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