Acetic Acid → 3-[4-Nitro-2-(trifluoromethyl)benzylidene]pentane-2,4-dione

HRID 1951387Notes

Reaction equation

HRID 1951387 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:4]=1[CH:5]=O.[CH3:16][C:17](=[O:22])[CH2:18][C:19](=[O:21])[CH3:20].C(O)(=O)C.N1CCCCC1>ClCCl>[N+:11]([C:9]1[CH:8]=[CH:7][C:4]([CH:5]=[C:18]([C:17](=[O:22])[CH3:16])[C:19](=[O:21])[CH3:20])=[C:3]([C:2]([F:15])([F:14])[F:1])[CH:10]=1)([O-:13])=[O:12]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 31261AcetylacetoneHCID 123911054-Nitro-2-(trifluoromethyl)benzaldehyde

Product 1

HCID 596030233-[4-Nitro-2-(trifluoromethyl)benzylidene]pentane-2,4-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1 g (4.56 mmol) of 2-trifluoromethyl-4-nitrobenzaldehyde, 0.51 ml (5.02 mmol) of 2,4-pentanedione, 0.4 ml (6.85 mmol) of acetic acid and 90 μl (0.91 mmol) of piperidine in 20 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 (1.28 g) is reacted in the next stage without further purification.

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 (1.28 g) is reacted in the next stage without further purification

Sources & evidence

ORD record
ord-83ac0246cdb4453b984f57c40650b2e2
Source dataset
uspto-grants-2013_03
Patent number
US08404709B2

Reaction notes

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