Malonic Acid → 5H-Dibenzo(A,D)cyclohepten-5-ylacetic acid

HRID 258205Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 258205
[CH:1]1[CH:15]=[C:14]2[C:4]([CH:5](O)[C:6]3[C:11]([CH:12]=[CH:13]2)=[CH:10][CH:9]=[CH:8][CH:7]=3)=[CH:3][CH:2]=1.C(O)(=O)[CH2:18][C:19]([OH:21])=[O:20]>>[CH:15]1[C:14]2[CH:13]=[CH:12][C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[CH:5]([CH2:18][C:19]([OH:21])=[O:20])[C:4]=2[CH:3]=[CH:2][CH:1]=1

Komponenten

3

Edukt 2

HCID 867Malonic AcidHCID 82577Dibenzosuberenol

Produkt 1

HCID 38305635H-Dibenzo(A,D)cyclohepten-5-ylacetic acid

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

A round bottom flask, equipped with a distillation apparatus, is charged with dibenzosuberenol (10.0 g, 48.01 mmol) and malonic acid (25.0 g, 240.08 mmol). The mixture is heated in a 160° C. oil bath. The solids melt. Gas bubbles form and water and acetic acid are distilled through the condenser. After 1.5 hours, the mixture is cooled to room temperature and dissolved in ethyl acetate. The organic solution is washed with brine and dried over MgSO4. The solvent is removed in vacuo to give an off white solid, which is recrystallized from hexane-ethyl acetate-(AcOEt)/1:1 to yield the title compound as white crystals, 10.2 g; mp167 °-168° C.

Aufarbeitung

  1. customA round bottom flask, equipped with a distillation apparatus
  2. distillationGas bubbles form and water and acetic acid are distilled through the condenser
  3. temperaturethe mixture is cooled to room temperature
  4. dissolutiondissolved in ethyl acetate
  5. washThe organic solution is washed with brine
  6. dry with materialdried over MgSO4
  7. customThe solvent is removed in vacuo
  8. customto give an off white solid, which
  9. customis recrystallized from hexane-ethyl acetate-(AcOEt)/1:1

Quellen und Nachweise

ORD-Eintrag
ord-9c52a335ded04ccf88e69b80d00deb49
Quelldatensatz
uspto-grants-1993_11
Patentnummer
US05264577

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