Acetic Acid → HCID 54153427, compound

HRID 255704Notes

Reaction equation

HRID 255704 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.N1CCCCC1>C1C=CC=CC=1.C(OCC)C>[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=[CH:13][C:12]([CH2:15][C:16](=[O:18])[CH3:17])=[O:14])([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 74493-NitrobenzaldehydeHCID 8082PiperidineHCID 31261Acetylacetone

Product 1

HCID 54153427HCID 54153427, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent

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 hr 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 3-(3-nitrobenzylidene)acetylacetone.

Workup

  1. temperaturewas refluxed for 1 hr 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-11d12fee261e49e2a5c4002fb5b6d288
Source dataset
uspto-grants-1987_10
Patent number
US04698340

Reaction notes

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