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

HRID 258205Notes

Reaction equation

HRID 258205 reaction equation
[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

Participants

3

Reactant 2

HCID 867Malonic AcidHCID 82577Dibenzosuberenol

Product 1

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

Conditions

Temperature
160 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-9c52a335ded04ccf88e69b80d00deb49
Source dataset
uspto-grants-1993_11
Patent number
US05264577

Reaction notes

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