Malonic Acid → 10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylacetic acid

HRID 1769555

Reaktionsgleichung

Reaktionsgleichung von HRID 1769555
[CH2:1]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9](O)[C:8]2[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:2]1.C(O)(=O)[CH2:18][C:19]([OH:21])=[O:20]>>[CH:4]1[C:3]2[CH2:2][CH2:1][C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[CH:9]([CH2:18][C:19]([OH:21])=[O:20])[C:8]=2[CH:7]=[CH:6][CH:5]=1

Komponenten

3

Edukt 2

HCID 867Malonic AcidHCID 14588Dibenzosuberol

Produkt 1

HCID 1266909110,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylacetic acid

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

A round-bottom flask, equipped with a distillation apparatus, is charged with dibenzosuberol (25.0 g, 0.119 mol) and malonic acid (61.9 g, 0,595 mol). The mixture is heated in an 160° C. oil bath. The solids melt. Gas bubbles form and water and acetic acid are distilled through the condenser. After 30 minutes, the mixture is cooled to room temperature and dissolved in ethyl acetate. The organic solution is washed with brine and dried (magnesium sulfate). The solvent is removed in vacuo to give an off-white solid, which is recrystallized from hexane-ethyl acetate/1:1 to yield the title compound as white crystals, 28.8 g; mp 164°-165° 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 (magnesium sulfate)
  7. customThe solvent is removed in vacuo
  8. customto give an off-white solid, which
  9. customis recrystallized from hexane-ethyl acetate/1:1

Quellen und Nachweise

ORD-Eintrag
ord-4441b60fa0804dd5b5079b6c34c06b41
Quelldatensatz
uspto-grants-1995_01
Patentnummer
US05380925

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