Ethanol → HCID 12902572, compound

HRID 648120Notes

Reaction equation

HRID 648120 reaction equation
[O:1]=[C:2]1[CH2:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[CH2:5][C:4]2[CH:13]=[C:14]([CH2:17][C:18]([OH:20])=[O:19])[CH:15]=[CH:16][C:3]1=2.[CH2:21](O)[CH3:22]>Cl>[O:1]=[C:2]1[CH2:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[CH2:5][C:4]2[CH:13]=[C:14]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:15]=[CH:16][C:3]1=2

Participants

4

Reactant 2

HCID 702EthanolHCID 12740029HCID 12740029, compound

Product 1

HCID 12902572HCID 12902572, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

In 3 ml of a 12% ethanol solution of hydrogen chloride was dissolved 0.14 g of 10,11-dihydro-11-oxo-5H-dibenzo[a,d]cycloheptene-3-acetic acid obtained in Example 3. The solution was heated under reflux for 30 minutes with stirring. After the reaction, the reaction mixture was cooled, and the solvent was distilled off. Water was added to the residue, and 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. Then, the ether was distilled off. The residue was chromatographed on a silica gel column using benzene as an eluent. From the eluate, 0.12 g of ethyl 10,11-dihydro-11-oxo-5H-dibenzo[a,d]cycloheptene-3-acetate was obtained as a slightly yellow oily substance.

Workup

  1. temperatureThe solution was heated
  2. temperatureunder reflux for 30 minutes
  3. customAfter the reaction
  4. temperaturethe reaction mixture was cooled
  5. distillationthe solvent was distilled off
  6. additionWater was added to the residue
  7. extractionthe mixture was extracted with ether
  8. washThe ethereal layer was washed with a saturated aqueous solution of sodium chloride
  9. dry with materialdried over anhydrous magnesium sulfate
  10. distillationThen, the ether was distilled off
  11. customThe residue was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-220a431662d7418fb50f8140f7e08860
Source dataset
uspto-grants-1983_10
Patent number
US04410716

Reaction notes

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