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

HRID 2308837Notes

Reaction equation

HRID 2308837 reaction equation
[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[CH:6]([CH:16](C(O)=O)[C:17]([OH:19])=[O:18])[C:5]=2[CH:4]=[CH:3][CH:2]=1.C1C=CC=CC=1>CCCCCC>[CH:12]1[C:8]2[CH2:9][CH2:10][C:11]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=3[CH:6]([CH2:16][C:17]([OH:19])=[O:18])[C:7]=2[CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 241BenzeneHCID 2018793310,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-malonic acid

Product 1

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

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

200 g of 10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-malonic acid are heated to 180° while stirring for 30 minutes. After cooling to 120°, the residue is treated with about 1 l of benzene and heated to boiling while stirring and under reflux until all crystallized-out material has again dissolved. Subsequently, the mixture is treated with 500 ml of hexane, cooled to about 10° while stirring and while cooling with ice, left to stand in the cold overnight and subsequently the crystal slurry obtained is removed by filtration under suction. After washing with petroleum ether and drying at 50° in a vacuum drying oven, there is obtained 10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-acetic acid as beige crystals of melting point 163°-165°.

Workup

  1. temperatureAfter cooling to 120°
  2. temperatureheated
  3. stirringwhile stirring
  4. temperatureunder reflux until all crystallized-out material
  5. dissolutionhas again dissolved
  6. temperaturecooled to about 10°
  7. stirringwhile stirring
  8. temperaturewhile cooling with ice
  9. waitleft
  10. customto stand in the cold overnight
  11. customsubsequently the crystal slurry obtained
  12. customis removed by filtration under suction
  13. washAfter washing with petroleum ether
  14. customdrying at 50° in a vacuum
  15. customdrying oven

Sources & evidence

ORD record
ord-a75afcb8a7bd4baca537d1f9fe475698
Source dataset
uspto-grants-1987_09
Patent number
US04691040

Reaction notes

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