Water → HCID 19972719, compound

HRID 1452303Notes

Reaction equation

HRID 1452303 reaction equation
[Mn]([O-])(=O)(=O)=O.[K+].[CH2:7]([C:10]1[C:19]2[O:18][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[C:16]([CH3:26])[C:15](=[O:27])[C:14]=2[CH:13]=[CH:12][CH:11]=1)[CH:8]=C.S(=O)(=O)(O)[OH:29].S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+].[OH2:42]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].ClCCl.C(O)(=O)C>[C:8]([CH2:7][C:10]1[C:19]2[O:18][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[C:16]([CH3:26])[C:15](=[O:27])[C:14]=2[CH:13]=[CH:12][CH:11]=1)([OH:29])=[O:42]

Participants

9

Reactant 5

HCID 962WaterHCID 1118Sulfuric AcidHCID 516875Potassium PermanganateHCID 656671Sodium PyrosulfiteHCID 232756214H-1-BENZOPYRAN-4-ONE, 3-METHYL-2-PHENYL-8-(2-PR

Product 1

HCID 19972719HCID 19972719, compound

Reagents, catalysts & solvents 3

HCID 21218Trioctylmethylammonium chlorideCatalyst2×HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

4.5 g of potassium permanganate was added portionwise within 1.5 hours under stirring at 0°-10° C., to a mixture of 2.76 g of 8-allyl-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran (P. Da Re, U.S. Pat. No. 3,350,411), 0.17 g of Aliquat 336® (methyltrioctylammonium chloride), 1.12 ml of acetic acid, 56 ml of dichloromethane, 3.2 ml of sulfuric acid (d=1.84) and 60 ml of water. Stirring was continued at room temperature for 5 hours. 3.4 g of sodium metabisulfite were added portionwise at 0°-5° C. within 15 minutes. The organic layer was separated, washed with water and extracted with 60 ml of 1N aqueous sodium hydroxide solution. The aqueous phase was acidified by addition of diluted hydrochloric acid and extracted with ethyl acetate. The organic phase was washed with water, dried on anhydrous sodium sulfate and, after filtration, evaporated to dryness in vacuo. The residue was treated with carbon tetrachloride and the solid was collected by suction to give 1 g of the title compound, m.p. 191°-192° C. (acetonitrile).

Workup

  1. customThe organic layer was separated
  2. washwashed with water
  3. extractionextracted with 60 ml of 1N aqueous sodium hydroxide solution
  4. additionThe aqueous phase was acidified by addition of diluted hydrochloric acid
  5. extractionextracted with ethyl acetate
  6. washThe organic phase was washed with water
  7. dry with materialdried on anhydrous sodium sulfate
  8. filtrationafter filtration
  9. customevaporated to dryness in vacuo
  10. additionThe residue was treated with carbon tetrachloride
  11. customthe solid was collected by suction

Sources & evidence

ORD record
ord-56968754dd0f4c589eedef6ee8d79564
Source dataset
uspto-grants-1997_02
Patent number
US05605896

Reaction notes

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