Cyclopentanone → Cyclopentanone, 2,5-bis[[4-(diethylamino)phenyl]methylene]-

HRID 1649193Notes

Reaction equation

HRID 1649193 reaction equation
[CH2:1]([N:3]([CH2:12][CH3:13])[C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1)[CH3:2].[C:14]1(=[O:19])[CH2:18][CH2:17][CH2:16][CH2:15]1>[OH-].[K+].CO>[CH2:1]([N:3]([CH2:12][CH3:13])[C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[C:15]2[CH2:16][CH2:17][C:18](=[CH:8][C:7]3[CH:10]=[CH:11][C:4]([N:3]([CH2:1][CH3:2])[CH2:12][CH3:13])=[CH:5][CH:6]=3)[C:14]2=[O:19])=[CH:6][CH:5]=1)[CH3:2]

Participants

5

Reactant 2

HCID 8452CyclopentanoneHCID 671144-(Diethylamino)benzaldehyde

Product 1

HCID 2734847Cyclopentanone, 2,5-bis[[4-(diethylamino)phenyl]methylene]-

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14797Potassium HydroxideSolvent

Procedure

About 110 g of p-diethylaminobenzaldehyde were dissolved in a solution of 80 g of potassium hydroxide in 1000 mL of methanol. About 26 g of cyclopentanone were added with stirring and the reaction mixture was heated under reflux on a steam bath for 3 hr. After chilling in the freezer, a solid precipitate was collected, washed with alcohol and recrystallized from a mixture of alcohol and acetonitrile. The title compound was confirmed by its NMR spectrum. This dye has an ε488 /MW of 188.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux on a steam bath for 3 hr
  3. temperatureAfter chilling in the freezer
  4. customa solid precipitate was collected
  5. washwashed with alcohol
  6. customrecrystallized from a mixture of alcohol and acetonitrile

Sources & evidence

ORD record
ord-1cb9571d656441d6924b21f635687fcc
Source dataset
uspto-grants-1983_11
Patent number
US04415621

Reaction notes

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