Hydrochloric Acid → 2,5-Dimethoxy3-methyl-6-[5-(2,5-dimethoxy-1,4-benzoquinon-3-yl)pentyl]1,4-benzoquinone

HRID 1588150Notes

Reaction equation

HRID 1588150 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]2[C:19]([O:20]COC)=[C:18]([O:24][CH3:25])[CH:17]=[C:16]([O:26]COC)[C:15]=2[O:30][CH3:31])=[C:7]([O:32]COC)[C:6]([O:36][CH3:37])=[C:5]([CH3:38])[C:4]=1[O:39]COC.O1CCCC1.C(O)(C)C.Cl.C(OCC)(=O)C.CCCCCC>O1CCCC1.C(O)(C)C>[CH3:37][O:36][C:6]1[C:7](=[O:32])[C:8]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]2[C:19](=[O:20])[C:18]([O:24][CH3:25])=[CH:17][C:16](=[O:26])[C:15]=2[O:30][CH3:31])=[C:3]([O:2][CH3:1])[C:4](=[O:39])[C:5]=1[CH3:38]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 136460751,4-Dimethoxy-2,5-bis(methoxymethoxy)-3-methyl-6-{5-[2,5-dimethoxy-3,6-bis(methoxymethoxy)phenyl]pentyl}benzeneHCID 21226206Ethyl acetate hexaneHCID 22597222Tetrahydrofuran 2-propanol

Product 1

HCID 136460832,5-Dimethoxy3-methyl-6-[5-(2,5-dimethoxy-1,4-benzoquinon-3-yl)pentyl]1,4-benzoquinone

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

426 Milligrams of 1,4-dimethoxy-2,5-bis(methoxymethoxy)-3-methyl-6-{5-[2,5-dimethoxy-3,6-bis(methoxymethoxy)phenyl]pentyl}benzene was dissolved in 5 ml of tetrahydrofuran and 5 ml of isopropanol, under nitrogen gas stream conditions, 1 ml of tetrahydrofuran-isopropanol (1:1) solution of 20% hydrogen chloride was added thereto, and the mixture was stirred at room temperature for 12 hours. The solvent was removed by evaporation under reduced pressure to obtain colorless powdery substance. This substance was dissolved, without being purified, in 20 ml of methanol, and a small amount of sodium hydrogen carbonate was added, then the mixture was heated at 60° C., and was stirred for 2 hours under oxygen gas stream condition. The solvent was removed by evaporation under reduced pressure, and the residue obtained was developed on a preparative thin layer chromatography (eluent: 40% ethyl acetate-n-hexane) to obtain 262 mg of 2,5-dimethoxy3-methyl-6-[5-(2,5-dimethoxy-1,4-benzoquinon-3-yl)pentyl]1,4-benzoquinone. Yellow powdery substance.

Workup

  1. customThe solvent was removed by evaporation under reduced pressure
  2. customto obtain colorless powdery substance
  3. dissolutionThis substance was dissolved
  4. customwithout being purified, in 20 ml of methanol
  5. additiona small amount of sodium hydrogen carbonate was added
  6. temperaturethe mixture was heated at 60° C.
  7. stirringwas stirred for 2 hours under oxygen gas stream condition
  8. customThe solvent was removed by evaporation under reduced pressure
  9. customthe residue obtained

Sources & evidence

ORD record
ord-62d5bf2fce604cf28965aa63d3429840
Source dataset
uspto-grants-1993_06
Patent number
US05220042

Reaction notes

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