Acetic Acid → 2-(4-Hydroxy-3-nitrobenzylidene)acetylacetone

HRID 255705

Reaction equation

HRID 255705 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[C:13]([CH2:16][C:17](=[O:19])[CH3:18])(=[O:15])[CH3:14].C(O)(=O)C.N1CCCCC1>C1C=CC=CC=1.C(OCC)C>[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH:14][C:13]([CH2:16][C:17](=[O:19])[CH3:18])=[O:15])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 181694-Hydroxy-3-nitrobenzaldehydeHCID 31261Acetylacetone

Product 1

HCID 570301622-(4-Hydroxy-3-nitrobenzylidene)acetylacetoneYield 85%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 4-hydroxy-3-nitrobenzaldehyde (43.5 g), acetylacetone (26 g), acetic acid (3.12 g) and piperidine (1.03 ml) in benzene (26 ml) was refluxed for 1 hours under azeotropic dehydration. To the reaction mixture was added 100 ml of diethyl ether. The mixture was washed with water (100 ml) and a saturated aqueous solution of sodium chloride (50 ml), dried over magnesium sulfate and evaporated in vacuo to afford 2-(4-hydroxy-3-nitrobenzylidene)acetylacetone (55.0 g).

Workup

  1. temperaturewas refluxed for 1 hours under azeotropic dehydration
  2. washThe mixture was washed with water (100 ml)
  3. dry with materiala saturated aqueous solution of sodium chloride (50 ml), dried over magnesium sulfate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-5b3fcac77b6a4e28a7a55070daa8b947
Source dataset
uspto-grants-1987_10
Patent number
US04698340

Linked notes

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