Oxygen → 2,2'-Ethylenebis(3,6-dimethoxy1,4-benzoquinone)

HRID 1588154Notes

Reaction equation

HRID 1588154 reaction equation
C[O:2][C:3]1[C:8]([O:9][CH2:10]OC)=[CH:7][C:6]([O:13]C)=[C:5]([O:15][CH2:16]OC)[C:4]=1[CH:19](O)[CH2:20][C:21]1[C:26]([O:27][CH2:28]OC)=[C:25]([O:31]C)[CH:24]=[C:23]([O:33][CH2:34]OC)[C:22]=1[O:37]C.C([SiH](CC)CC)C.C(=O)([O-])O.[Na+].O=O>FC(F)(F)C(O)=O.CO.C(OCC)(=O)C.CCCCCC>[CH2:19]([C:4]1[C:3](=[O:2])[C:8]([O:9][CH3:10])=[CH:7][C:6](=[O:13])[C:5]=1[O:15][CH3:16])[CH2:20][C:21]1[C:22](=[O:37])[C:23]([O:33][CH3:34])=[CH:24][C:25](=[O:31])[C:26]=1[O:27][CH3:28]

Participants

8

Reactant 4

HCID 977OxygenHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 197572131,2-Bis[2,5-dimethoxy-3,6-bis(methoxymethoxy)phenyl]ethanol

Product 1

HCID 197571732,2'-Ethylenebis(3,6-dimethoxy1,4-benzoquinone)Yield 67.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6422Trifluoroacetic acidSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

Under ice-cooling conditions, 302 mg of 1,2-bis[2,5-dimethoxy-3,6-bis(methoxymethoxy)phenyl]ethanol was dissolved in 5 ml of trifluoroacetic acid, then 0.4 ml of triethylsilane was added to the solution. This mixture was stirred under ice-cooling conditions for 2 hours. After concentrated the reaction mixture, benzene was added and the mixture was further treated under a reduced pressure. The residue thus obtained was dissolved in 5 ml of methanol, and a catalytic amount of sodium hydrogen carbonate was added thereto, and oxygen gas was blown into the reaction mixture. 2 Hours later, the reaction mixture was filtered, and the filtrate was concentrated under a reduced pressure. The residue obtained was treated by means of a thin layer chromatography (adsorbent: silica gel, manufactured by E. Merck A. G., size: 20 cm×20 cm, thickness: 2 mm, 2 plates were used, developping solvent: 30% ethyl acetate-n-hexane) to obtain 132 mg of 2,2'-ethylenebis(3,6-dimethoxy1,4-benzoquinone). Yellow oily substance.

Workup

  1. temperaturecooling conditions for 2 hours
  2. concentrationAfter concentrated the reaction mixture, benzene
  3. additionwas added
  4. additionthe mixture was further treated under a reduced pressure
  5. customThe residue thus obtained
  6. filtration2 Hours later, the reaction mixture was filtered
  7. concentrationthe filtrate was concentrated under a reduced pressure
  8. customThe residue obtained
  9. additionwas treated by means of a thin layer chromatography (adsorbent

Sources & evidence

ORD record
ord-138345eb4ab64a9eaa3530d2c1a0049b
Source dataset
uspto-grants-1993_06
Patent number
US05220042

Reaction notes

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