Hydrochloric Acid → HCID 13714572, compound

HRID 1588157Notes

Reaction equation

HRID 1588157 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9]COC)=[CH:7][C:6]([O:13][CH3:14])=[C:5]([O:15]COC)[C:4]=1[CH2:19][CH2:20][CH2:21][C:22]1[C:27]([O:28]COC)=[C:26]([O:32][CH3:33])[CH:25]=[C:24]([O:34]COC)[C:23]=1[O:38][CH3:39].Cl.C(=O)([O-])O.[Na+].O=O>O1CCCC1.C(O)(C)C.CO>[CH3:39][O:38][C:23]1[C:24](=[O:34])[CH:25]=[C:26]([O:32][CH3:33])[C:27](=[O:28])[C:22]=1[CH2:21][CH2:20][CH2:19][C:4]1[C:5](=[O:15])[C:6]([O:13][CH3:14])=[CH:7][C:8](=[O:9])[C:3]=1[O:2][CH3:1]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 977OxygenHCID 516892Sodium BicarbonateHCID 19757258HCID 19757258, compound

Product 1

HCID 13714572HCID 13714572, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

169 Milligrams of 2,2'-trimethylenebis[1,4-dimethoxy-3,6-bis(methoxymethoxy)benzene] was dissolved in 2 ml of tetrahydrofuran and 2 ml of isopropanol, then to this solution was added 0.4 ml of a tetrahydrofuranisopropanol (1:1) solution containing 20% (by weight) of hydrogen chloride, then the mixture was stirred at room temperature for 1 day under argon gas stream condition. The solvent was removed by evaporation under reduced pressure, then the residue obtained was dissolved in 20 ml of methanol, and a small amount of sodium hydrogen carbonate was added to this solution, and stirred at room temperature for 30 minutes with blowing oxygen gas thereinto. The solvent was removed by evaporation, the resulting residue was treated by means on a preparative thin layer chromatography (thickness 1 mm, adsorbent: silica gel), and developped with a mixed solvent of ethyl acetate-n-hexane (1:1) to obtain 50 mg of crude product. The crude product was recrystallized from ethanol to obtain 20.4 mg of 2,2'-trimethylenebis(3,6-dimethoxy1,4-benzoquinone). Yellow fine needles crystals.

Workup

  1. customThe solvent was removed by evaporation under reduced pressure
  2. customthe residue obtained
  3. customThe solvent was removed by evaporation
  4. additionthe resulting residue was treated by means on a preparative thin layer chromatography (thickness 1 mm, adsorbent
  5. customto obtain 50 mg of crude product
  6. customThe crude product was recrystallized from ethanol

Sources & evidence

ORD record
ord-0d9ad5c683c2430dba32906f3f224286
Source dataset
uspto-grants-1993_06
Patent number
US05220042

Reaction notes

Loading…