Acetic Acid → Diethyl 2-[(3-formylphenyl)methylene]propane-1,3-dioate

HRID 30447

Reaktionsgleichung

Reaktionsgleichung von HRID 30447
[C:1]1([CH:9]=O)[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=[O:8])[CH:2]=1.C([C:13](CC)([C:17]([O-:19])=[O:18])[C:14]([O-:16])=[O:15])C.N1CCC[CH2:24][CH2:23]1.[CH3:28][C:29](O)=O>C1(C)C=CC=CC=1>[CH:7]([C:3]1[CH:2]=[C:1]([CH:9]=[C:13]([C:17]([O:19][CH2:28][CH3:29])=[O:18])[C:14]([O:16][CH2:23][CH3:24])=[O:15])[CH:6]=[CH:5][CH:4]=1)=[O:8]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 34777IsophthalaldehydeHCID 69515632,2-Diethylpropanedioate

Produkt 1

HCID 59789754Diethyl 2-[(3-formylphenyl)methylene]propane-1,3-dioate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

Benzene 1,3 dicarbaldehyde (1 eq) is dissolved in toluene, and diethylmalonate (1 eq) is added, followed by piperidine (0.1 eq) and AcOH (0.1 eq). The flask is equipped with a Dean Stark trap and the reaction mixture is refluxed overnight. The reaction mixture is cooled down to room temperature, washed with water, 2% aq HCl, sat. aq NaHCO3, brine, and dried. The solvent is evaporated under reduced pressure and the product 32 is isolated by column chromatography on silicagel.

Aufarbeitung

  1. customThe flask is equipped with a Dean Stark trap
  2. temperaturethe reaction mixture is refluxed overnight
  3. washwashed with water, 2% aq HCl, sat. aq NaHCO3, brine
  4. customdried
  5. customThe solvent is evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-fd79de5b16c441b29e7acf5015ddc480
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423148B2

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