Acetic Acid → 4-(2-Acetyl-3-oxo-1-butenyl)benzonitrile

HRID 1951377Notes

Reaction equation

HRID 1951377 reaction equation
[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1)=O.[CH3:11][C:12](=[O:17])[CH2:13][C:14](=[O:16])[CH3:15].C(O)(=O)C.N1CCCCC1>ClCCl>[C:14]([C:13]([C:12](=[O:17])[CH3:11])=[CH:1][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1)(=[O:16])[CH3:15]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 31261AcetylacetoneHCID 660424-Cyanobenzaldehyde

Product 1

HCID 3674534-(2-Acetyl-3-oxo-1-butenyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.3 g (17.5 mmol) of 4-formylbenzonitrile, 1.98 ml (19.29 mmol) of 2,4-pentanedione, 1 ml (26 mmol) of acetic acid and 0.34 ml (3.5 mmol) of piperidine in 40 ml of anhydrous dichloromethane are stirred under reflux with a water trap for 24 h. After cooling, the reaction solution is washed successively with saturated sodium bicarbonate solution and saturated sodium chloride solution. The organic phase is dried over magnesium sulfate and concentrated. The residue is recrystallized from diethyl ether. 3.18 g (85% of theory) of the title compound are obtained as a pale brown solid.

Workup

  1. temperatureunder reflux with a water trap for 24 h
  2. temperatureAfter cooling
  3. washthe reaction solution is washed successively with saturated sodium bicarbonate solution and saturated sodium chloride solution
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue is recrystallized from diethyl ether

Sources & evidence

ORD record
ord-4bdd19e40c9348fd815fbb2abf86bdab
Source dataset
uspto-grants-2013_03
Patent number
US08404709B2

Reaction notes

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