Hydrochloric Acid → HCID 13714571, compound

HRID 1588155Notes

Reaction equation

HRID 1588155 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][CH2:22][C:23]1[C:28]([O:29]COC)=[C:27]([O:33][CH3:34])[CH:26]=[C:25]([O:35]COC)[C:24]=1[O:39][CH3:40].Cl.C(=O)([O-])O.[Na+].O=O>C(O)(C)C.O1CCCC1.O1CCCC1.C(O)(C)C.CO.C1C=CC=CC=1>[CH3:40][O:39][C:24]1[C:25](=[O:35])[CH:26]=[C:27]([O:33][CH3:34])[C:28](=[O:29])[C:23]=1[CH2:22][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

10

Reactant 4

HCID 313Hydrochloric AcidHCID 977OxygenHCID 516892Sodium BicarbonateHCID 19757195HCID 19757195, compound

Product 1

HCID 13714571HCID 13714571, compound

Reagents, catalysts & solvents 5

HCID 241BenzeneSolventHCID 887MethanolSolventHCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolventHCID 22597222Tetrahydrofuran 2-propanolSolvent

Procedure

355 Milligrams of 2,2'-tetramethylenebis[1,4-dimethoxy-3,6-bis(methoxymethoxy)benzene] was dissolved in a mixed solvent of 8 ml of isopropanol with 4 ml of tetrahydrofuran, to this solution was added 1.2 ml of solution prepared by dissolving 10% (by weight/weight) of hydrogen chloride in a mixed solvent of tetrahydrofuran-isopropanol (1:1), and the mixture was stirred at room temperature for 12 hours. The reaction mixture was concentrated under reduced pressure, to the residue obtained was added benzene, and further concentrated under 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 thereinto. 2 Hours later, the reaction mixture was filtered, and the filtrate was concentrated under reduced pressure, and the residue obtained was purified by means of a silica gel chromatography (diameter 2 cm×length 5 cm, eluent: 30%-ethyl acetate-n-hexane mixed solvent, adsorbent: "Wakogel C-200") to obtain 120 mg of 2,2'-tetramethylenebis(3,6-dimethoxy-1,4 -benzoquinone). Yellow needles crystals.

Workup

  1. customprepared
  2. concentrationThe reaction mixture was concentrated under reduced pressure, to the residue
  3. customobtained
  4. concentrationfurther concentrated under reduced pressure
  5. customThe residue thus obtained
  6. filtration2 Hours later, the reaction mixture was filtered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customthe residue obtained
  9. customwas purified by means of a silica gel chromatography (diameter 2 cm×length 5 cm, eluent: 30%-ethyl acetate-n-hexane mixed solvent, adsorbent: "Wakogel C-200")

Sources & evidence

ORD record
ord-b4a4ca9dc79149b5a96046b369c605b7
Source dataset
uspto-grants-1993_06
Patent number
US05220042

Reaction notes

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