4-Methylcyclohexanone → HCID 4546474, compound

HRID 647213Notes

Reaction equation

HRID 647213 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].[CH3:14][CH:15]1[CH2:20][CH2:19][C:18](=[O:21])[CH2:17][CH2:16]1.[O-][CH2:23][CH3:24].[Na+]>C(O)C>[CH2:1]([N:3]([CH2:12][CH3:13])[C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[C:17]2[CH2:16][CH:15]([CH3:14])[CH2:20][C:19](=[CH:8][C:7]3[CH:10]=[CH:11][C:4]([N:3]([CH2:23][CH3:24])[CH2:1][CH3:2])=[CH:5][CH:6]=3)[C:18]2=[O:21])=[CH:6][CH:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 115254-MethylcyclohexanoneHCID 671144-(Diethylamino)benzaldehydeHCID 2723922Sodium ethoxide

Product 1

HCID 4546474HCID 4546474, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 50 ml of anhydrous ethanol were dissolved 35.4 g of p-diethylaminobenzaldehyde and 11.2 g of 4-methylcyclohexanone, 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 5 hours. The reaction mixture was cooled, and the crystals thus precipitated were collected by filtration, and then recrystallized from toluene, to obtain 30.2 g of 2,6-bis(4'-diethylaminobenzal)-4-methylcyclohexanone (m.p. 169° C.).

Workup

  1. additionwas added dropwise to the resulting solution
  2. customthe resulting mixture was subjected to reaction
  3. temperatureunder reflux for 5 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-153691200be64e89a5716978f7fc7231
Source dataset
uspto-grants-1983_10
Patent number
US04407927

Reaction notes

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