Benzaldehyde → 2-Benzylidenecyclohexanone

HRID 1737174Notes

Reaction equation

HRID 1737174 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[OH-].[Na+].[C:12]1(=[O:18])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH:1](=[C:13]1[CH2:14][CH2:15][CH2:16][CH2:17][C:12]1=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 962WaterHCID 7967CyclohexanoneHCID 14798Sodium Hydroxide

Product 1

HCID 989262-BenzylidenecyclohexanoneYield 28%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

A 500-ml four-necked flask equipped with a thermometer was charged with 53 g of benzaldehyde, 25 ml of water and 1 g of sodium hydroxide, to which 68 g of cyclohexanone were added dropwise at 30° C. over 30 minutes. The resultant mixture was stirred for 1 hour at the same temperature. After neutralizing the reaction mixture to separate liquid layers from each other, the resultant reaction product was dissolved in 500 ml of toluene. To the solution, 0.5 g of PTS (p-toluenesulfonic acid) was added to conduct azeotropic dehydration for 3 hours in a 1-liter four-necked flask equipped with a Dean-Stark trap and a thermometer. After cooling, the residue was neutralized and washed with water, and the resultant organic layer was dried and concentrated, thereby obtaining 119 g of a crude product. This product was purified by column chromatography to obtain 24 g (yield: 28%) of 2-benzylidenecyclohexanone.

Workup

  1. customA 500-ml four-necked flask equipped with a thermometer
  2. additionwere added dropwise at 30° C. over 30 minutes
  3. customto separate liquid layers from each other, the resultant
  4. customreaction product
  5. customfor 3 hours
  6. customequipped with a Dean-Stark trap
  7. temperatureAfter cooling
  8. washwashed with water
  9. customthe resultant organic layer was dried
  10. concentrationconcentrated
  11. customobtaining 119 g of a crude product
  12. customThis product was purified by column chromatography

Sources & evidence

ORD record
ord-a165918cd26a441a9dc0447259023052
Source dataset
uspto-grants-1999_10
Patent number
US05962403

Reaction notes

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