4-Methylbenzaldehyde → Diethyl [(4-methylphenyl)methylidene]propanedioate

HRID 742329Notes

Reaction equation

HRID 742329 reaction equation
[C:1]1([CH3:9])[CH:6]=[CH:5][C:4]([CH:7]=O)=[CH:3][CH:2]=1.[C:10]([O:18][CH2:19][CH3:20])(=[O:17])[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].N1CCCCC1>C1C=CC=CC=1.O>[CH3:9][C:1]1[CH:6]=[CH:5][C:4]([CH:7]=[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:10]([O:18][CH2:19][CH3:20])=[O:17])=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 77254-MethylbenzaldehydeHCID 7761Diethyl MalonateHCID 8082Piperidine

Product 1

HCID 641322Diethyl [(4-methylphenyl)methylidene]propanedioateYield 99%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 962WaterSolvent

Procedure

A mixture of 19.6 mL (166.4 mmol) of p-tolualdehyde, 23.8 mL (158.8 mmol) of diethyl malonate, 0.5 mL of piperidine and 50 mL of benzene was heated at reflux for 18 h using a Dean-Stark water separator. The mixture was allowed to cool to room temperature, benzene was added and it was washed with water (2×), 1N HCl (2×) and NaHCO3. The aqueous phase was extracted with ethyl acetate, the organic phase was dried and the solvent was removed, to yield 41.2 g of the desired product (yield: 99%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 h
  3. washit was washed with water (2×), 1N HCl (2×) and NaHCO3
  4. extractionThe aqueous phase was extracted with ethyl acetate
  5. customthe organic phase was dried
  6. customthe solvent was removed

Sources & evidence

ORD record
ord-8dd22717a9c34c7d9e17795525dd0d25
Source dataset
uspto-grants-1996_09
Patent number
US05554624

Reaction notes

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