Cyclohexanone → Cyclohexanone, 2,6-bis[[4-(diethylamino)phenyl]methylene]-

HRID 647215Notes

Reaction equation

HRID 647215 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:20])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.[O-][CH2:22][CH3:23].[Na+]>C(O)C>[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][CH2:18][C:19](=[CH:8][C:7]3[CH:10]=[CH:11][C:4]([N:3]([CH2:22][CH3:23])[CH2:1][CH3:2])=[CH:5][CH:6]=3)[C:14]2=[O:20])=[CH:6][CH:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 7967CyclohexanoneHCID 671144-(Diethylamino)benzaldehydeHCID 2723922Sodium ethoxide

Product 1

HCID 3385046Cyclohexanone, 2,6-bis[[4-(diethylamino)phenyl]methylene]-

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 25 ml of anhydrous ethanol were dissolved 17.7 g of p-diethylaminobenzaldehyde and 4.9 g of cyclohexanone, and 10 ml of 10% ethanolic solution of sodium ethoxide was added dropwise to the resulting solution, and the resulting mixture was subjected to reaction under reflux for 12 hours. The reaction mixture thus obtained was cooled, and the crystals thus precipitated were collected by filtration and recrystallized from toluene, to obtain 12.8 g of 2,6-bis(4'-diethylaminobenzal)cyclohexanone (m.p. 167° C.).

Workup

  1. additionwas added dropwise to the resulting solution
  2. customthe resulting mixture was subjected to reaction
  3. temperatureunder reflux for 12 hours
  4. customThe reaction mixture thus obtained
  5. temperaturewas cooled
  6. customthe crystals thus precipitated
  7. filtrationwere collected by filtration
  8. customrecrystallized from toluene

Sources & evidence

ORD record
ord-bba1d053dd8e49fabd93c6dd23ad5421
Source dataset
uspto-grants-1983_10
Patent number
US04407927

Reaction notes

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