Potassium periodate → 7-Acetoxy-8-methoxycoumarin-6-acetaldehyde

HRID 1448515Notes

Reaction equation

HRID 1448515 reaction equation
[C:1]([O:4][C:5]1[C:14]([O:15][CH3:16])=[C:13]2[C:8]([CH:9]=[CH:10][C:11](=[O:17])[O:12]2)=[CH:7][C:6]=1[CH2:18][CH:19]=C)(=[O:3])[CH3:2].I([O-])(=O)(=O)=[O:22].[K+]>[Os](=O)(=O)(=O)=O.CCOC(C)=O.O>[C:1]([O:4][C:5]1[C:14]([O:15][CH3:16])=[C:13]2[C:8]([CH:9]=[CH:10][C:11](=[O:17])[O:12]2)=[CH:7][C:6]=1[CH2:18][CH:19]=[O:22])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 516896Potassium periodateHCID 218145017-Acetoxy-6-allyl-8-methoxycoumarin

Product 1

HCID 537672567-Acetoxy-8-methoxycoumarin-6-acetaldehyde

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 22728543Water ethylacetateSolvent

Procedure

A solution of 0.274 g. (0.001 mole) of 7-acetoxy-6-allyl-8-methoxycoumarin in 10 ml. EtOAc/water, 1:1 was treated with 0.8 g. (0.0033 mole) of potassium periodate and 0.5 ml. of a 10% aqueous solution of osmium tetroxide (10 mg. OsO4 /ml H2O). The reactants were stirred at 25° for 5.0 hours. The organic layer was separated, and the aqueous phase was further extracted with ethyl acetate. The organic extracts were combined, dried over sodium sulfate, and evaporated to yield pure 7-acetoxy-8-methoxycoumarin-6-acetaldehyde as a colorless oil.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous phase was further extracted with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-381186712d4749caa2f5329203fc6098
Source dataset
uspto-grants-1979_12
Patent number
US04180659

Reaction notes

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