4-Chlorobenzaldehyde → 5-[(4-Chlorophenyl)methylidene]-2,2-dimethylcyclopentan-1-one

HRID 1769108Notes

Reaction equation

HRID 1769108 reaction equation
[OH-].[Na+].[CH3:3][C:4]1([CH3:10])[CH2:8][CH2:7][CH2:6][C:5]1=[O:9].[Cl:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=1>C(O)C>[CH3:3][C:4]1([CH3:10])[CH2:8][CH2:7][C:6](=[CH:16][C:15]2[CH:18]=[CH:19][C:12]([Cl:11])=[CH:13][CH:14]=2)[C:5]1=[O:9]

Participants

5

Reactant 3

HCID 77264-ChlorobenzaldehydeHCID 14798Sodium HydroxideHCID 1382862,2-Dimethylcyclopentanone

Product 1

HCID 534210215-[(4-Chlorophenyl)methylidene]-2,2-dimethylcyclopentan-1-oneYield 59.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

10% strength sodium hydroxide solution (100 cc) is added to a mixture of 2,2-dimethylcyclopentanone (10 g) and 4-chlorobenzaldehyde (13.8 g) in ethanol (100 cc) at 0° C. After 10 minutes, the thick slurry is filtered and the solid washed and then dried. 2,2-Dimethyl-5-(4-chlorobenzylidene)-1-cyclopentanone (12.5 g), m.p. 120° C., is obtained.

Workup

  1. filtrationthe thick slurry is filtered
  2. washthe solid washed
  3. customdried

Sources & evidence

ORD record
ord-350ac0bf60ea446d9ad05b837621011b
Source dataset
uspto-grants-1995_01
Patent number
US05380743

Reaction notes

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