4-(Diethylamino)benzaldehyde → 2,6-Bis(4'-diethylaminobenzal)-4-ethylcyclohexanone

HRID 647214

Reaction equation

HRID 647214 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].[CH2:14]([CH:16]1[CH2:21][CH2:20][C:19](=[O:22])[CH2:18][CH2:17]1)[CH3:15].[O-][CH2:24][CH3:25].[Na+]>C(O)C>[CH2:1]([N:3]([CH2:12][CH3:13])[C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[C:18]2[CH2:17][CH:16]([CH2:14][CH3:15])[CH2:21][C:20](=[CH:8][C:7]3[CH:10]=[CH:11][C:4]([N:3]([CH2:24][CH3:25])[CH2:1][CH3:2])=[CH:5][CH:6]=3)[C:19]2=[O:22])=[CH:6][CH:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 671144-(Diethylamino)benzaldehydeHCID 795064-EthylcyclohexanoneHCID 2723922Sodium ethoxide

Product 1

HCID 544620222,6-Bis(4'-diethylaminobenzal)-4-ethylcyclohexanone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 50 ml of anhydrous ethanol were dissolved 35.4 g of p-diethylaminobenzaldehyde and 12.6 g of 4-ethylcyclohexanone, and 20 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 was cooled, and the crystals thus precipitated were collected by filtration and then recrystallized from toluene, to obtain 15.8 g of 2,6-bis(4'-diethylaminobenzal)-4-ethylcyclohexanone (m.p. 141° 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. temperatureThe reaction mixture was cooled
  5. customthe crystals thus precipitated
  6. filtrationwere collected by filtration
  7. customrecrystallized from toluene

Sources & evidence

ORD record
ord-dca57614efa24155a882bd0f60287b76
Source dataset
uspto-grants-1983_10
Patent number
US04407927

Linked notes

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