Ethanol → HCID 12789591, compound

HRID 355107Notes

Reaction equation

HRID 355107 reaction equation
C([OH:3])C.[OH-].[K+].[O:6]=[C:7]1[CH2:13][C:12]2[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=2[O:10][C:9]2[CH:18]=[CH:19][C:20]([CH2:22][C:23](N)=[O:24])=[CH:21][C:8]1=2>O>[O:6]=[C:7]1[CH2:13][C:12]2[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=2[O:10][C:9]2[CH:18]=[CH:19][C:20]([CH2:22][C:23]([OH:24])=[O:3])=[CH:21][C:8]1=2

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 13134778HCID 13134778, compound

Product 1

HCID 12789591HCID 12789591, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a mixture of 2 ml of water, 2 ml of ethanol and 0.4 g of potassium hydroxide was added 100 mg of (10,11-dihydro-11-oxo dibenzo[b,f]oxepin-2-yl)-acetamide, and the resulting mixture was refluxed with stirring for 5 hours. After cooling, to this was added water, and the mixture was washed with ethyl acetate. The aqueous layer was acidified with hydrochloric acid and extracted with ethyl acetate. The extract was washed with a saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was distilled off to obtain yellow crystals, which were chromatographed over 9 g of silica gel and eluted with chloroform/methanol (50/1), thereby obtaining 77 mg (yield: 77%) of (10,11-dihydro-11-oxo dibenzo-[b,f]oxepin-2-yl)-acetic acid. This acid was recrystallized from acetone/n-hexane to give colorless crystals having a melting point of 155.7°-157° C.

Workup

  1. temperaturethe resulting mixture was refluxed
  2. temperatureAfter cooling
  3. washthe mixture was washed with ethyl acetate
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with a saturated sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off
  8. customto obtain yellow crystals, which
  9. customwere chromatographed over 9 g of silica gel
  10. washeluted with chloroform/methanol (50/1)

Sources & evidence

ORD record
ord-6dc3c8bc0c6c48ccadd89fa372a32b6a
Source dataset
uspto-grants-1983_03
Patent number
US04377702

Reaction notes

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