Acetic Acid → 3-((3-Nitrophenyl)methylene)-2,4-pentanedione

HRID 4674

Reaction equation

HRID 4674 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O)([O-:3])=[O:2].[C:12]([CH2:15][C:16](=[O:18])[CH3:17])(=[O:14])[CH3:13].C(O)(=O)C.C(OCC)C>C1C=CC=CC=1.N1CCCCC1>[C:12]([C:15](=[CH:7][C:6]1[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)[C:16]([CH3:17])=[O:18])(=[O:14])[CH3:13]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 3283Diethyl EtherHCID 74493-NitrobenzaldehydeHCID 31261Acetylacetone

Product 1

HCID 959903-((3-Nitrophenyl)methylene)-2,4-pentanedioneYield 53.5%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 241BenzeneSolvent

Procedure

A mixture of 3-nitrobenzaldehyde (20 g), acetylacetone (13.25 g), acetic acid (1.58 g), and piperidine (0.45 g) in benzene (20 ml) was refluxed for 1 hour under azeotropic dehydration. To the reaction mixture was added diethyl ether (100 ml). The mixture was washed with water (50 ml) and a saturated aqueous solution of sodium chloride (50 ml) successively, dried over magnesium sulfate, and evaporated in vacuo. The residual substance was recrystallized from ether to afford 1-acetyl-1-(3-nitrobenzyliden)acetone(16.5 g).

Workup

  1. temperaturewas refluxed for 1 hour under azeotropic dehydration
  2. washThe mixture was washed with water (50 ml)
  3. dry with materiala saturated aqueous solution of sodium chloride (50 ml) successively, dried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residual substance was recrystallized from ether

Sources & evidence

ORD record
ord-48a09d41fff04695972f49c0700533bc
Source dataset
uspto-grants-1988_02
Patent number
US04727073

Linked notes

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