Acetic Acid → Methyl 5-(2-nitrophenyl)-3-oxopent-4-enoate

HRID 2351942Notes

Reaction equation

HRID 2351942 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=O)([O-:3])=[O:2].[C:12]([O:18][CH3:19])(=[O:17])[CH2:13][C:14]([CH3:16])=[O:15].N1CCCCC1.C(O)(=O)C>C1C=CC=CC=1>[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=[CH:16][C:14](=[O:15])[CH2:13][C:12]([O:18][CH3:19])=[O:17])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7757Methyl acetoacetateHCID 8082PiperidineHCID 111012-Nitrobenzaldehyde

Product 1

HCID 53723829Methyl 5-(2-nitrophenyl)-3-oxopent-4-enoateYield 98%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

o-Nitrobenzaldehyde (7.6 g, 0.05 mole) and methyl acetoacetate (5.8 g, 0.05 mole) are dissolved in benzene (40 ml), and thereto are added piperidine (0.2 ml) and acetic acid (0.6 ml), and the mixture is refluxed for 5 hours. The produced water is removed, and when a stoichiometic amount of water is distilled off, the reaction is stopped. After completion of the reaction, the reaction mixture is washed with 5% hydrochloric acid and then with water, and the solvent is distilled off under reduced pressure to give the title compound (12.2 g, yield 98%) as a brown oil.

Workup

  1. temperaturethe mixture is refluxed for 5 hours
  2. customThe produced water is removed
  3. distillationwhen a stoichiometic amount of water is distilled off
  4. customAfter completion of the reaction
  5. washthe reaction mixture is washed with 5% hydrochloric acid
  6. distillationwith water, and the solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-b57d384df9ce43ceb72c67800f3f58dd
Source dataset
uspto-grants-1989_10
Patent number
US04874773

Reaction notes

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