Acetic Acid → HCID 19804623, compound

HRID 1682131Notes

Reaction equation

HRID 1682131 reaction equation
C([C:4]1[C:5]([O:20][CH3:21])=[CH:6][C:7]2[C:13](=[O:14])[C:12]3[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=3[CH2:10][O:9][C:8]=2[CH:19]=1)C=C.CC(C)=O.[Mn]([O-])(=O)(=O)=O.[K+].S([O-])(O)=O.[Na+].[C:37]([OH:40])(=[O:39])[CH3:38]>O>[CH3:21][O:20][C:5]1[C:4]([CH2:38][C:37]([OH:40])=[O:39])=[CH:19][C:8]2[O:9][CH2:10][C:11]3[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=3[C:13](=[O:14])[C:7]=2[CH:6]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 180AcetoneHCID 516875Potassium Permanganate2×HCID 19804622HCID 19804622, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 19804623HCID 19804623, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
15 °C

Procedure

19.5 grams of 3-allyl-2-methoxy-6,11-dihydrodibenz[b,e]oxepin-11-one obtained in the above Reference Example were dissolved in a mixed liquid consisting of 400 ml of acetone, 150 ml of acetic acid and 150 ml of water and incorporated in portions with 44 g of potassium permanganate at a temperature of 10°-15 C. over a period of 4 hours, after which the whole was agitated at 15° C. for 1 hour. After the end of the reaction, the unreacted potassium permanganate was decomposed with sodium hydrogen sulfite, after which the insoluble materials in the reaction mixture were filtered out and then the filtrate obtained was evaporated to dryness under a reduced pressure. The residue obtained was incorporated with water to precipitate crystals which were then filtered off. The crystals so filtered off were adsorbed in silica gel packed in a column and developed with a 7:1 chloroform-methanol mixed solution (silica gel column chromatography). The resulting effluent was freed from the solvent by distillation, after which the residue obtained was recrystallized from ethyl acetate thereby to obtain 5.6 g of 2-methoxy-6,11-dihydro-11-oxodibenz[b,e]oxepin-3-acetic acid in the form of colorless needle-like crystals.

Workup

  1. dissolutionwere dissolved in a mixed liquid
  2. customAfter the end of the reaction
  3. filtrationafter which the insoluble materials in the reaction mixture were filtered out
  4. customthe filtrate obtained
  5. customwas evaporated to dryness under a reduced pressure
  6. customThe residue obtained
  7. customto precipitate crystals which
  8. filtrationwere then filtered off
  9. filtrationThe crystals so filtered off
  10. distillationThe resulting effluent was freed from the solvent by distillation
  11. customafter which the residue obtained
  12. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-e0b30c8dd9f34deea1db3eac6bb1b4c5
Source dataset
uspto-grants-1992_12
Patent number
US05175286

Reaction notes

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