Hydrochloric Acid → HCID 10964852, compound

HRID 617805Notes

Reaction equation

HRID 617805 reaction equation
[O:1]=[C:2]1[C:11]2[CH2:10][CH:9]=[C:8]([O:12]C)[CH2:7][C:6]=2[CH2:5][CH2:4][CH2:3]1.Cl.C(OCC)(=O)C>O1CCCC1>[C:2]1(=[O:1])[C:11]2[CH2:10][CH2:9][C:8](=[O:12])[CH2:7][C:6]=2[CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 11805303HCID 11805303, compound

Product 1

HCID 10964852HCID 10964852, compoundYield 76.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6.8 g (38.2 mmol) of 1,2,3,4,5,8-hexahydro-1-oxo-6-methoxynaphthalene was dissolved in 50 ml of tetrahydrofuran and 5 ml of 1 N hydrochloric acid was added thereto. After stirring at room temperature for 1 hour, ethyl acetate was added thereto. Then the reaction mixture was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. After concentrating, a small amount of a mixture of n-hexane with ethyl acetate (1:1) was added thereto and the obtained mixture was cooled in a dry ice-ether bath. The precipitate thus formed was recovered by filtration and washed with a small amount of n-hexane to thereby give 4.8 g of the title compound.

Workup

  1. washThen the reaction mixture was washed with a saturated aqueous solution of sodium chloride
  2. dry with materialdried over magnesium sulfate
  3. concentrationAfter concentrating
  4. additiona small amount of a mixture of n-hexane with ethyl acetate (1:1)
  5. additionwas added
  6. temperaturethe obtained mixture was cooled in a dry ice-ether bath
  7. customThe precipitate thus formed
  8. filtrationwas recovered by filtration
  9. washwashed with a small amount of n-hexane

Sources & evidence

ORD record
ord-4599bbfab22847909407ceb350836dfe
Source dataset
uspto-grants-1999_09
Patent number
US05952335

Reaction notes

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