Hydrochloric Acid → HCID 12740030, compound

HRID 648124Notes

Reaction equation

HRID 648124 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]=[CH:14][C:15]([CH2:17][C:18]([O:20]C)=[O:19])=[CH:16][C:3]1=2.[OH-].[Na+].O.Cl>CO>[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]=[CH:14][C:15]([CH2:17][C:18]([OH:20])=[O:19])=[CH:16][C:3]1=2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 12902573HCID 12902573, compound

Product 1

HCID 12740030HCID 12740030, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 2 ml of methanol was dissolved 0.1 g of methyl 10,11-dihydro-11-oxo-5H-dibenzo[a,d]cycloheptene-2-acetate obtained in Example 16, and 6 ml of a 10% aqueous solution of sodium hydroxide was added. The mixture was heated under reflux for 2 hours with stirring. After the reaction, the reaction mixture was cooled, and water was added. The mixture was acidified with 10% hydrochloric acid, and the precipitated solid was extracted with ether. The ethereal layer was washed with a saturated aqueous solution of sodium chloride and then dried over anhydrous magnesium sulfate. The ether was distilled off. Recrystallization of the residue from a mixture of ether and n-hexane afforded 0.082 g of 10,11-dihydro-11-oxo-5H-dibenzo[a,d]cycloheptene-2-acetic acid as colorless needle-like crystals having a melting point of 171° to 173° C.

Workup

  1. additionwas added
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 2 hours
  4. customAfter the reaction
  5. temperaturethe reaction mixture was cooled
  6. extractionthe precipitated solid was extracted with ether
  7. washThe ethereal layer was washed with a saturated aqueous solution of sodium chloride
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationThe ether was distilled off
  10. customRecrystallization of the residue
  11. additionfrom a mixture of ether and n-hexane

Sources & evidence

ORD record
ord-e0797fb5505d43c1b641b180c99c17ea
Source dataset
uspto-grants-1983_10
Patent number
US04410716

Reaction notes

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