4-Methylbenzaldehyde → 1,4-Pentadien-3-one, 1-(4-methylphenyl)-5-phenyl-

HRID 2050617Notes

Reaction equation

HRID 2050617 reaction equation
[CH:1](=[CH:8][C:9](=[O:11])[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:12]1([CH3:20])[CH:17]=[CH:16][C:15]([CH:18]=O)=[CH:14][CH:13]=1.[OH-].[Na+]>C(O)C.O>[C:2]1([CH:1]=[CH:8][C:9](=[O:11])[CH:10]=[CH:20][C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 77254-MethylbenzaldehydeHCID 14798Sodium HydroxideHCID 159094-Phenyl-3-Buten-2-one

Product 1

HCID 46515071,4-Pentadien-3-one, 1-(4-methylphenyl)-5-phenyl-Yield 72.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 146.0 g (1.0 mole) of benzalacetone and 122.0 g (1.02 mole) 4-tolualdehyde (Compound II-A) was dissolved in 750 ml ethanol, and the solution was diluted with 200 ml water. With stirring, at room temperature, all at once, 100 ml of 10% NaOH solution were added. After 1.5 hours the thick, cream precipitate was filtered off, resuspended in 1 liter 20% ethanol in water, refiltered, sucked dry and recrystallized from ethanol/ethyl acetate to give 180 g of 1-phenyl-5-(4-tolyl)-1,4-pentadiene-3-one (Compound IV-A). The product structure was confirmed by field desorption mass spectrometry (FDMS) and infrared (IR) spectrometry.

Workup

  1. filtrationAfter 1.5 hours the thick, cream precipitate was filtered off
  2. customsucked dry
  3. customrecrystallized from ethanol/ethyl acetate

Sources & evidence

ORD record
ord-6e2dffdb721849ad830c1b44c04f14a1
Source dataset
uspto-grants-1991_05
Patent number
US05013849

Reaction notes

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