Benzaldehyde → 1-Phenyl-1,4-pentanedione

HRID 1708599Notes

Reaction equation

HRID 1708599 reaction equation
CN(C)C=O.[CH:6](=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C-]#N.[Na+].[CH:17]([C:19]([CH3:21])=[O:20])=[CH2:18]>O>[C:7]1([C:6](=[O:13])[CH2:18][CH2:17][C:19](=[O:20])[CH3:21])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 6228Dimethylformamide3×HCID 6570Methyl vinyl ketoneHCID 8929Sodium Cyanide

Product 1

HCID 1363711-Phenyl-1,4-pentanedioneYield 40%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
35 °C

Procedure

To 1200 ml of dimethylformamide (DMF) containing 3 moles of benzaldehyde and heated at 35° C., a mixed solution of 0.3 mole of sodium cyanide and 2400 ml of DMF was added dropwise in 30 minutes, and the reaction was carried out for further 30 minutes with stirring. To the reaction solution, a mixed solution of 2.25 moles of methyl vinyl ketone and 2400 ml of DMF was added dropwise in 30 minutes, and the reaction was carried out for further 1 hour. After the reaction, water was poured into the reaction solution, followed by extraction with chloroform. The obtained chloroform solution was washed with dilute sulfuric acid, saturated aqueous solution of sodium bicarbonate, and water in this order, and dried over anhydrous sodium sulfate. The solvent was removed by distillation. The resulting residue was distilled under reduced pressure to give a fraction of pale yellow liquid of 1-phenyl-1,4-pentanedione having a boiling point of 124°-127° C./0.15 mmHg (yield 40% ).

Workup

  1. waitthe reaction was carried out for further 1 hour
  2. additionwas poured into the reaction solution
  3. extractionfollowed by extraction with chloroform
  4. washThe obtained chloroform solution was washed with dilute sulfuric acid, saturated aqueous solution of sodium bicarbonate, and water in this order
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was removed by distillation
  7. distillationThe resulting residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-9eb1c49f4f0f42ccb0ccd4e6859312a1
Source dataset
uspto-grants-1994_10
Patent number
US05359085

Reaction notes

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