4-Chlorobenzaldehyde → 1-(p-Chlorophenyl)-4-phenyl-7-(m-chlorophenyl)-1,6-heptadien-3-one

HRID 1076314Notes

Reaction equation

HRID 1076314 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1.[C:12]1([CH:18]([CH2:22][CH:23]=[CH:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[CH:26]=2)[C:19](=[O:21])[CH3:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(O)C>[Cl:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[CH:20][C:19](=[O:21])[CH:18]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:22][CH:23]=[CH:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[CH:26]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 77264-ChlorobenzaldehydeHCID 14798Sodium HydroxideHCID 537053773-Phenyl-6-(m-chlorophenyl)-5-hexen-2-one

Product 1

HCID 543508231-(p-Chlorophenyl)-4-phenyl-7-(m-chlorophenyl)-1,6-heptadien-3-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A sodium hydroxide solution (7.5 ml., 20%) is added to a solution of p-chlorobenzaldehyde (17.86 g., 0.127 mole) and 3-phenyl-6-(m-chlorophenyl)-5-hexen-2-one (36.11 g., 0.127 mole) in ethanol (360 ml.) with stirring. The gum that separates on continued stirring is chromatographed (benzene) through a silica gel column to obtain the product as a very viscous oil (opaque).

Workup

  1. stirringThe gum that separates on continued stirring
  2. customis chromatographed (benzene) through a silica gel column
  3. customto obtain the product as a very viscous oil (opaque)

Sources & evidence

ORD record
ord-43382d9ef0204527956b23fffb63c0ea
Source dataset
uspto-grants-1976_05
Patent number
US03956374

Reaction notes

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