Water → 2-(3-Nitrophenylmethylidene)-3-oxobutanoic acid, 1-methylpropyl ester

HRID 580500Notes

Reaction equation

HRID 580500 reaction equation
[C:1]([O:7][CH:8]([CH2:10][CH3:11])[CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[N+:12]([C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=O)([O-:14])=[O:13].N1CCCCC1.O>C1C=CC=CC=1.C(O)(=O)C>[N+:12]([C:15]1[CH:16]=[C:17]([CH:18]=[C:2]([C:3](=[O:4])[CH3:5])[C:1]([O:7][CH:8]([CH3:9])[CH2:10][CH3:11])=[O:6])[CH:20]=[CH:21][CH:22]=1)([O-:14])=[O:13]

Participants

7

Reactant 4

HCID 962WaterHCID 74493-NitrobenzaldehydeHCID 8082PiperidineHCID 139498sec-Butyl acetoacetate

Product 1

HCID 571863202-(3-Nitrophenylmethylidene)-3-oxobutanoic acid, 1-methylpropyl ester

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 241BenzeneSolvent

Procedure

A solution of sec-butyl acetoacetate (5.0 g, 0.031 moles), 3-nitrobenzaldehyde (4.7 g, 0.031 moles), 0.5 ml of piperidine and 0.5 ml of acetic acid in 50 ml of benzene was heated at reflux for one hour collecting 1 eq. of water. The cooled solution, in ethyl acetate, was washed with sodium hydrogen carbonate, potassium hydrogen sulfate and brine, dried and evaporated to give 9.2 g of the title A compound as a dark oil.

Workup

  1. temperatureat reflux for one hour
  2. washThe cooled solution, in ethyl acetate, was washed with sodium hydrogen carbonate, potassium hydrogen sulfate and brine
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-3d729ccdb69949698addee97894c8725
Source dataset
uspto-grants-1988_06
Patent number
US04753946

Reaction notes

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