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

HRID 258201Notes

Reaction equation

HRID 258201 reaction equation
[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

Participants

3

Reactant 2

HCID 867Malonic AcidHCID 14588Dibenzosuberol

Product 1

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

Conditions

Temperature
160 °C

Procedure

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.

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 (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

Sources & evidence

ORD record
ord-67075623cdb94f95b22545428d5c9080
Source dataset
uspto-grants-1993_11
Patent number
US05264577

Reaction notes

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