Acetic Acid → Ethyl 2-(3-nitrobenzylidene)-3-oxobutanoate

HRID 1648852Notes

Reaction equation

HRID 1648852 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]([O:18][CH2:19][CH3:20])(=[O:17])[CH2:13][C:14]([CH3:16])=[O:15].N1CCCCC1.C(O)(=O)C>C1C=CC=CC=1>[C:14]([C:13](=[CH:7][C:6]1[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)[C:12]([O:18][CH2:19][CH3:20])=[O:17])(=[O:15])[CH3:16]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 74493-NitrobenzaldehydeHCID 8082PiperidineHCID 8868Ethyl Acetoacetate

Product 1

HCID 367507Ethyl 2-(3-nitrobenzylidene)-3-oxobutanoateYield 69.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A reaction mixture containing m-nitrobenzaldehyde (151 g; 1.0 mole), ethyl acetoacetate (130 g; 1.0 mole), piperidine (4 mL) and glacial acetic acid (12 mL) in 200 mL benzene was refluxed for 2.5 hr while removing water (19 mL) by means of a Dean Stark trap. The dark brown reaction solution was allowed to cool to room temperature and was then water washed several times and concentrated in vacuo to give a dark yellow solid. This solid was recrystallized from ethanol to yield 182 g (69% yield) of yellow solid, m.p. 103°-106° C. Literature m.p.: S. Ruhemann, J. Chem. Soc., Vol 83, 717 (1903)--m.p. 110° C.

Workup

  1. temperaturewas refluxed for 2.5 hr
  2. customwhile removing water (19 mL) by means of a Dean Stark trap
  3. concentrationwater washed several times and concentrated in vacuo
  4. customto give a dark yellow solid
  5. customThis solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-8873359c3ae34b908b04f1329d89e34f
Source dataset
uspto-grants-1983_11
Patent number
US04414213

Reaction notes

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