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

HRID 1076326Notes

Reaction equation

HRID 1076326 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]([CH3:31])[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]([CH3:31])[CH:26]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 77264-ChlorobenzaldehydeHCID 14798Sodium HydroxideHCID 537406993-Phenyl-6-(m-methylphenyl)-5-hexen-2-one

Product 1

HCID 541666091-(p-Chlorophenyl)-4-phenyl-7-(m-methylphenyl)-1,6-heptadien-3-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 20% sodium hydroxide solution (5 ml.) is added to a stirred solution of p-chlorobenzaldehyde(14 g., 0.1 mole) and 3-phenyl-6-(m-methylphenyl)-5-hexen-2-one (25.24 g., 0.096 mole) in ethanol (250 ml.). The yellowish solid that separates on continued stirring is collected, washed with cold ethanol, and air-dried, yield 34.9 g., m.p. 89°-93°C. Recrystallization from ethanaol produces material with m.p. 95°-98°C.

Workup

  1. customis collected
  2. washwashed with cold ethanol
  3. customair-dried
  4. customRecrystallization from ethanaol
  5. customproduces material with m.p. 95°-98°C.

Sources & evidence

ORD record
ord-b50f224f8c71407b9e65d84aa72903df
Source dataset
uspto-grants-1976_05
Patent number
US03956374

Reaction notes

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