Hydrogen Bromide → HCID 12740030, compound

HRID 648125Notes

Reaction equation

HRID 648125 reaction equation
Br.C[O:3][C:4]1[C:5]2[CH:18]=[C:17]([CH2:19][C:20]([O:22]C)=[O:21])[CH:16]=[CH:15][C:6]=2[CH2:7][C:8]2[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=2[CH:10]=1>O>[O:3]=[C:4]1[CH2:10][C:9]2[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=2[CH2:7][C:6]2[CH:15]=[CH:16][C:17]([CH2:19][C:20]([OH:22])=[O:21])=[CH:18][C:5]1=2

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 12740032HCID 12740032, compound

Product 1

HCID 12740030HCID 12740030, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Six milliliters of 47% hydrobromic acid was added to 0.32 g of methyl 11-methoxy-5H-dibenzo[a,d]cycloheptene-2-acetate obtained in Example 11, and the mixture was stirred at 100° to 125° C. for 30 minutes. After the reaction, the reaction mixture was cooled, and water was added. The mixture was extracted with ether. The ethereal layer was washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. The ether was distilled off. Recrystallization of the residue from a mixture of methanol and n-hexane afforded 0.22 g of 10,11-dihydro-11-oxo-5H-dibenzo[a,d]cycloheptene-2-acetic acid as colorless needle-like crystals.

Workup

  1. customAfter the reaction
  2. temperaturethe reaction mixture was cooled
  3. extractionThe mixture was extracted with ether
  4. washThe ethereal layer was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe ether was distilled off
  7. customRecrystallization of the residue
  8. additionfrom a mixture of methanol and n-hexane

Sources & evidence

ORD record
ord-3aaef8658cb44262886581b58e825ada
Source dataset
uspto-grants-1983_10
Patent number
US04410716

Reaction notes

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